FUNGICIDAL FUSED BICYCLIC PYRIMIDINONES

Abstract: This invention pertains to compounds of Formulae (I), (II), and (III) including all geometric and stereoisomers, N-oxides, agriculturally-suitable salts thereof, agricultural compositions containing them and their use as fungicides, wherein: Q is O or S; and n, R<1>, R<2>, R<3>, R<4>, R<5>, R<6>, R<7>, R<8>, and R<9> are described in the text.

Description: TITLE FUNGICIDAL FUSED BICYCLIC PYRUVUDINONES This invention relates to certain 4(3H)-quinazolinones, their agriculturally suitable salts and compositions, and methods of their use as general or selective fungicides, in particular for the control of cereal powdery mildew both preventive and curative. U.S. 3,755,582 and U.S. 3,867,384 disclose certain 4(3H)-quinazolinone fungicides. These patents, however, do not specifically disclose the compounds of the present invention. SUMMARY OF THE INVENTION This invention comprises compounds of Formulae I, π, and in including all geometric and stereoisomers, N-oxides, agriculturally-suitable salts thereof, agricultural compositions containing them and their use as fungicides: wherein: n is 0, 1 or 2; Q is independently O or S; R 1 is C3-C10 al yl; C3-C5 cycloalkyl; C4-C10 alkenyl; C4-C10 alkynyl; C Cχo haloalkyl; C3-C10 haloalkenyl; C3-C10 haloalkynyl; C2-C10 alkoxyalkyl; C2-C10 alkylthioalkyl; C2-C-10 alkylsulfinylalkyl; C2-C10 alkylsulfonylalkyl; C5-C10 cycloalkylalkyl; C4-C*to alkenyloxyalkyl; C4-C10 alkynyloxyalkyl; C4-C10 (cycloalkyl)oxyalkyl; C4-C10 alkenylthioalkyl; C4-C10 al ynylthioalkyl; Cg-C j o (cycloalkyl)thioalkyl; C2-C1 Q haloalkoxyalkyl; 4-C10 haloalkenyloxyalkyl; C4-C1 haloalkynyloxyalkyl; C4-C10 alkoxyalkenyl; C4-C10 alkoxyalkynyl; C4-C10 alkylthioalkenyl; C4-C10 al ylthioalkynyl; C4-C 10 trialkylsilylal yl; CJ-CIQ alkyl substituted with NR 1 ;l R 12 , nitro, cyano, or phenyl optionally substituted with R 14 , R 15 , and R 16 ; C r C 10 alkoxy; C r C 10 haloalkoxy; C r C 10 alkylthio; C r C 10 haloalkylthio; NR 1 ^ 12 ; orpyridyl, furanyl, thienyl, nφhthyl, benzofuranyl, benzothienyl, or quinolinyl each optionally substituted with R 14 , R 15 , and Rl6 ; R 2 is C 3 -C 10 alkyl; C 6 -C 7 cycloalkyl; C 3 -C 10 alkenyl; C 3 -C 10 alkynyl; C C 10 haloalkyl; C3-C 1Q haloalkenyl; C3-C1 Q haloalkynyl; C2-C10 alkoxyalkyl; C 2 -C 10 alkylthioalkyl; C2-CJO alkylsulfinylalkyl; C 2 -Cιø alkylsulfonylalkyl; C4-C10 cycloalkylalkyl; C4-C10 alkenyloxyalkyl; C4-C10 alkynyloxyalkyl; C4-C10 (cycloalkyl)oxyalkyl; C4-CJ0 alkenylthioalkyl; C4-C10 alkynylthioalkyl; Cg-C j ø (cycloalkyl)thioalkyl; C2-Cιø haloalkoxyalkyl; C4-C10 haloalkenyloxyalkyl; C4-C10 haloalkynyloxyalkyl; C4-C10 alkoxyalkenyl; C4-C10 alkoxyalkynyl; C4-C10 alkylthioalkenyl; C4-C10 all^lthioalkynyl; C4-C10 trialkylsilylalkyl; C3-C10 cyanoalkyl; C2-C10 nitroalkyl; C r C 10 alkyl substituted with CO 2 R π , NR π R 12 , or phenyl optionally substituted with R 13 , R 15 , and R 16 ; phenyl optionally substituted withR 13 , R!5, andR^; -N^R^R 11 ; or -NR-^Rl 2 ; or R 1 and R 2 are taken together to form -CH 2 (CH 2 ) m CH2-; m is 1-4; R 3 is halogen; C r C 8 alkyl; C 3 -C 8 cycloalkyl; C 2 -C 8 alkenyl; C 2 -C 8 alkynyl; C r C 8 haloalkyl; C3~C 8 haloalkenyl; C3~C 8 haloalkynyl; C j -Cg alkoxy; Cj-Cg haloalkoxy; C3-C 8 alkenyloxy; C3~C alkynyloxy; Cj-C 8 alkylthio; C3-C alkenylthio; C3-C 8 alkynylthio; C j -C 8 alkylsulfinyl; C j -C alkylsulfonyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C 2 -C 8 alkylsulfinylalkyl; C 2 -C 8 alkylsulfonylalkyl; C 4 -C 8 cycloalkylalkyl; C 3 -C 8 trialkylsilyl; nitro; NR 11 R 12 ; C5~C 8 trialkylsilylalkynyl; or phenyl optionally substituted with at least one RI 3 ; R 4 is hydrogen; halogen; -C4 alkyl; C1-C4 haloalkyl; C1-C4 alkoxy; or C1-C4 haloalkoxy; R 5 is C3-C5 alkyl; C 7 -C 10 alkyl; C 4 -C 7 alkenyl; C3-C5 alkynyl; C r C 10 haloalkyl; C5-C10 haloalkenyl; C3-C10 haloalkynyl; C2-C10 alkoxyalkyl other than methoxypropyl; C2-C10 alkylthioalkyl; C2-C10 alkylsulfinylalkyl; C2-C10 alkylsulfonylalkyl; C4-C1 cycloalkylalkyl; C4-C10 alkenyloxyalkyl; C4-C10 alkynyloxyalkyl; C4-C10 (cycloalkyl)oxyalkyl; C4-C10 alkenylthioalkyl; C 4 -C 10 alkynylthioalkyl; C 6 -C 10 (cycloalkyl)thioalkyl; C 2 -C 10 haloalkoxyalkyl; C4-C10 haloalkenyloxyalkyl; C4-C10 haloalkynyloxyalkyl; C4-C10 alkoxyalkenyl; C4-C10 alkoxyalkynyl; C4-C10 alkylthioalkenyl; C4-C10 alkylthioalkynyl; C4-C10 trialkylsilylalkyl; CJ-CJO alkyl substituted with NR 1 :l R 12 , nitro, or phenyl optionally substituted with at least one of R 14 , R 15 , and R 16 ; C 2 -C 10 alkyl substituted with cyano; C r C 10 alkoxy; C r C 10 haloalkoxy; C r C 10 alkylthio; C r C 10 haloalkylthio; NR n R 12 ; or phenyl, furanyl, thienyl, naphthyl, benzofuranyl, or benzothienyl each optionally substituted with R 14 , R 15 , and R 16 ; R 6 is C 3 -C 10 alkyl; C 3 -C 7 alkenyl; C 3 -C 10 alkynyl; C r C 10 haloalkyl; C 3 -C 10 haloalkenyl; C3-C1 Q haloalkynyl; C3-C10 alkoxyalkyl other than propoxymethyl; C2-C10 alkylthioalkyl; C2-C10 alkylsulfinylalkyl; C2-C10 alkylsulfonylalkyl; C4-C1 Q cycloalkylalkyl; C4-C10 alkenyloxyalkyl; C4-C10 alkynyloxyalkyl; C4-C10 (cycloalkyl)oxyalkyl; C4-C1 alkenylthioalkyl; C 4 -C 10 alkynylthioalkyl; C 6 -C 10 (cycloalkyl)thioalkyl; C2-C-10 haloalkoxyalkyl; C4-C10 haloalkenyloxyalkyl; C4-C10 haloalkynyloxyalkyl; C4-C10 alkoxyalkenyl; C4-C10 alkoxyalkynyl; C4-C10 alkylthioalkenyl; C4-C10 alkylthioalkynyl; C4-CK ) trialkylsilylalkyl; C5-C1 Q cyanoalkyl; C2-C nitroalkyl; or C 3 -C 10 alkyl substituted with CO 2 R π , NR π R 12 , or phenyl optionally substituted with R 13 , R 15 , and R 16 ; or phenyl optionally substituted with R 13 , R 15 , and R 16 ; or R 5 and R 6 are taken together to form -CH 2 (CH 2 ) m CH 2 -; R 7 is C3-C 1 ø alkyl; C3-C7 cycloalkyl; C4-C7 alkenyl; propynyl; C _ 5 .,-C ~ 1ι0υ a ~lkynyl; C2-C 10 haloalkyl; C3-C10 haloalkenyl; C3-C-10 haloalkynyl; C2-C 1-K0 ] alkoxyalkyl; C2-C-K) alkylthioalkyl; C2-C10 alkylsulfinylalkyl; C2-C 1 1 0 0 alkylsulfonylalkyl; C4-C-10 alkenyloxyalkyl; C4-C10 alkynyloxyalkyl; C4-C ~10 (cycloalkyl)oxyalkyl; C4-C1 Q alkenylthioalkyl; C4-C10 alkynylthioalkyl; Cg-C j o (cycloalkyl)thioalkyl; C2-C10 haloalkoxyalkyl; C4-C10 haloalkenyloxyalkyl; C4-C10 haloalkynyloxyalkyl; C4-C10 alkoxyalkenyl; C4-C10 alkoxyalkynyl; C4-C10 alkylthioalkenyl; C4-C10 alkylthioalkynyl; C -C 10 trialkylsilylalkyl; C r C 10 alkyl substituted with NR 1;l R 12 or nitro; C2-C1 0 alkyl substituted with cyano; CI-CJO alkoxy; CJ-CJ Q haloalkoxy; C r C 10 alkylthio; CJ-CH ) haloalkylthio; NR 12 R 17 ; or phenyl, pyridyl, furanyl thienyl, naphthyl, benzofiiranyl, benzothienyl, or quinolinyl each optionally substituted with R 14 , R 15 , and R 16 ; R 8 is hydrogen; C r C 4 alkyl; or -C(=O)R 10 ; R 9 is hydrogen; C2-C10 alkyl; C3-C7 cycloalkyl; C~-CI Q alkenyl; C^- I Q alkynyl; yCiQ haloalkyl; CyCi Q haloalkenyl; C3-C10 haloalkynyl; C3-C10 alkoxyalkyl other than butoxyethyl; C2-C10 alkylthioalkyl; C2-C10 alkylsulfinylalkyl; C2-C10 alkylsulfonylalkyl; C4-C10 cycloalkylalkyl; C4-C10 alkenyloxyalkyl; C4-C10 alkynyloxyalkyl; C4-CJO (cycloalkyl)oxyalkyl; C4-C10 alkenylthioalkyl; C4-C 1Q alkynylthioalkyl; Cg-C j ø (cycloalkyl)thioalkyl; C2-C10 haloalkoxyalkyl; C4-C10 haloalkenyloxyalkyl; C -C 10 haloalkynyloxyalkyl; C4-C 10 alkoxyalkenyl; C4-C-10 alkoxyalkynyl; C4- 0 alkylthioalkenyl; C4-CJ0 alkylthioalkynyl; C4-C10 trialkylsilylalkyl; C r C 10 alkyl substituted with NR n R 12 ; C 4 -C 10 cyanoalkyl; C 2 -C 10 nitroalkyl; Cj-C alkyl substituted with CO2R 11 ; pyridyl, furanyl, thienyl, or naphthyl each optionally substituted with R 14 , R 15 , and R 16 ; -N=CR 11 R 11 ; -NR 12 R 17 ; -OR 12 ; or -NC(=Q)NR 11 R 12 ; or R 3 and R 4 are both iodine and R 9 is phenyl optionally substituted with R 14 , R 15 , and R 16 ; or R 7 and R 9 are taken together to form -CH 2 (CH 2 ) m CH 2 -; R 10 is hydrogen; C r C 4 alkyl; C r C 4 alkoxy; or NR 1 :l R 12 ; R 11 is independently hydrogen; C1-C4 alkyl; or phenyl optionally substituted with at least one R 13 ; R 12 is independently hydrogen; C j -C alkyl; or phenyl optionally substituted with at least one R 13 ; or R 11 and R 12 are taken together to form -CH2CH2CH2CH2-, -CH 2 (CH 2 )3CH 2 -, -CH 2 CH 2 OCH 2 CH 2 -, -CH 2 CH(Me)CH 2 CH(Me)CH 2 -, or -CH 2 CH(Me)OCH(Me)CH 2 -; R 13 is independently halogen; C1-C4 alkyl; C* ( -C4 alkoxy; C1-C4 haloalkyl; nitro; or cyano; R 14 is independently ^-Cg alkyl; Cj-Cg alkoxy; Cj-Cg haloalkyl; halogen; C2-C alkynyl; C-pCg thioalkyl; phenyl or phenoxy each optionally substituted with at least one R 13 ; cyano; nitro; Cj-Cg haloalkoxy; Cj-Cg haloalkylthio; C2-C alkenyl; C2-Cg haloalkenyl; acetyl; CO2Me; or N(Cj-C2 alkyl)2; R 15 is independently methyl; ethyl; methoxy; methylthio; halogen; or trifluoromethyl; R 16 is independently halogen; and R 17 is independently Cj-C 8 alkyl; or phenyl optionally substituted with at least one RI 3 . DETAILED DESCRIPTION OF THE INVENTION In the above recitations, the term "alkyl", used either alone or in compound words such as "alkylthio," "haloalkyl," or "alkylthioalkyl" denotes straight-chain or branched alkyl; e.g., methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl, hexyl, etc. isomers. "Cycloalkyl" denotes cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. The term "cycloalkyloxyalkyl" denotes the cycloalkyl groups linked through an oxygen atom to an alkyl chain. Examples include cyclopentyloxymethyl and cyclohexyloxybutyl. The term "cycloalkylthioalkyl" are the cycloalkyl groups linked through a sulfur atom to an alkyl chain; e.g., cyclopropylthiopentyl. "Cycloalkylalkyl" denotes a cycloalkyl ring attached to a branched or straight-chain alkyl; e.g. cyclopropylmethyl and cyclohexylbutyl. "Alkenyl" denotes straight chain or branched alkenes; e.g., 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl , pentenyl, hexenyl, etc. isomers. Alkenyl also denotes polyenes such as 1,3-hexadiene and 2,4,6-heptatriene. "Alkynyl" denotes straight chain or branched alkynes; e.g., ethynyl, 1 -propynyl, 3-propynyl and the different butynyl, pentynyl, hexynyl, etc. isomers. "Alkynyl" can also denote moieties comprised of multiple triple bonds; e.g., 2,7-octadiyne and 2,5,8- decatriyne. "Alkoxy" denotes methoxy, ethoxy, .-propyloxy, isopropyloxy and the different butoxy, pentoxy, hexyloxy, etc. isomers. "Alkoxyalkenyl" and "alkoxyalkynyl" denoted groups in which the alkoxy group is bonded throught the oxygen atom to an alkenyl or alkynyl group, respectively. Examples include CH3OCH2CH=CH and (CH^CHOC^C≡CGH^. The corresponding sulfur derivatives are denoted "alkylthioalkenyl and "alkylthioalkynyl." Examples of the former include CH 3 SCH 2 CH=CH and CH 3 CH 2 SCH2(CH 3 )CH=CHCH 2 , and an example of the latter is CH 3 CH2CH 2 CH2SCH 2 C≡C. "Alkenyloxy" denotes straight chain or branched alkenyloxy moieties. Examples of alkenyloxy include H 2 C=CHCH 2 O, (CH 3 ) 2 C=CHCH 2 O, (CH 3 )CH=CHCH 2 O, (CH 3 )CH=C(CH3)CH 2 O and CH2=CHCH2CH2θ. "Alkenylthio" denotes the similar groups wherein the oxygen atom is replaced with a sulfur atom; e.g., H2C=CHCH2S and (CH 3 )CH=C(CH 3 )CH 2 S. The term "alkenyloxyalkyl" denotes groups in which the alkenyloxy moiety is attached to an alkyl group. Examples include H 2 C=CHCH2OCH 2 CH2, H 2 C=CHCH 2 OCH(CH3)CH2, etc. "Alkenylthioalkyl" denotes the alkenylthio moieties bonded to an alkyl group. Examples include H 2 C=CHCH 2 SCH(CH3)CH(CH3) and (CH 3 )CH=C(CH 3 )CH 2 SCH2. "Alkynyloxy" denotes straight or branched alkynyloxy moieties. Examples include HC≡CCH 2 O, CH 3 C≡CCH 2 O and CH 3 C≡CCH 2 CH 2 O. "Alkynyloxyalkyl" denotes alkynyloxy moieties bonded to alkyl groups; e.g., CH3CSCCH2OCH2CH2 and HC≡CCH 2 OCH(CH 3 )CH 2 . "Alkynylthioalkyl" denotes alkynylthio moieties bonded to alkyl groups. Example include CH3C≡CCH 2 SCH 2 CH2 and CH 3 C≡CCH2CH 2 SCH(CH3)CH2. "Alkylthio" denotes methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. "Alkylthioalkyl" denotes alkylthio groups attached to an alkyl chain; e.g., CH 3 CH 2 SCH 2 CH(CH3) and (CH 3 ) 2 CHSCH 2 . "Alkylsulfinyl" denotes both enantiomers of an alkylsulfinyl group. For example, CH 3 S(O), CH 3 CH 2 S(O), CH 3 CH 2 CH 2 S(O), (CH 3 ) 2 CHS(O) and the different butylsulfinyl, pentylsulfinyl and hexylsufinyl isomers. "Alkylsulfinylalkyl" denotes alkylsulfinyl groups attached to an alkyl chain; e.g., CH 3 CH 2 S(O)CH 2 CH(CH3) and (CH 3 ) 2 CHS(O)CH 2 . Examples of "alkylsulfonyl" include CH 3 S(O) 2 , CH 3 CH 2 S(O) 2 , CH 3 CH 2 CH 2 S(O) 2 , (CH 3 ) 2 CHS(O) 2 and the different butylsulfonyl, pentylsulfonyl and hexylsulfonyl isomers. "Alkylsulfonylalkyl" denotes alkylsulfonyl groups attached to an alkyl chain; e.g., CH 3 CH 2 S(O) 2 CH 2 CH(CH 3 ) and (CH 3 ) 2 CHS(O) 2 CH 2 . The term "halogen", either alone or in compound words such as "haloalkyl", denotes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl", said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of "haloalkyl" include F 3 C, CICH2, CF 3 CH 2 and CF 3 CF 2 . Examples of "haloalkenyl" include (C1) 2 C=CHCH 2 and CF3CH 2 CH=CHCH 2 . "Haloalkenyloxyalkyl" denotes haloalkenyl groups bonded to oxygen and in turn bonded to alkyl groups. Examples include CF 3 CH 2 CH=CHCH 2 OCH 2 and (Cl) 2 C=CHCH 2 OCH 2 CH 2 . Examples of "haloalkynyl" include HC≡CCHCl, CF 3 C≡C, CC1 3 C≡C and FCH 2 C≡CCH 2 . "Haloalkynyloxyalkyl" denotes haloalkynyl groups bonded through an oxygen atom to an alkyl moiety. Examples include CF 3 C≡CCH 2 OCH 2 CH 2 , ClCH 2 C≡CCH 2 CH 2 OCH(CH 3 ), etc. Examples of "haloalkoxy" include CF 3 O, CCl 3 CH 2 O, CF 2 HCH 2 CH 2 O and CF 3 CH 2 O. "Haloalkoxyalkyl" denotes haloalkoxy groups bonded to straight-chain or branched alkyl groups; e.g., CF 2 HCH 2 CH 2 OCH 2 CH 2 , CCl 3 CH 2 OCH(CH 3 ) and CF 3 OCH 2 . "Trialkylsilyl" designates a group with three alkyl groups bonded to silicon; e.g., (CH 3 ) 3 Si and t-Bu(CH 3 ) 2 Si. "Trialkylsilylalkyl" denotes trialkylsilyl groups bonded to another straight-chain or branched alkyl group. Examples include (CH3)3SiCH 2 and t-Bu(CH 3 ) 2 SiCH 2 CH(CH 3 )CH 2 . The total number of carbon atoms in a substituent group is indicated by the "C*-Cj" prefix where i and j are numbers from 1 to 10. For example, C j -C 3 alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C 2 alkoxyalkoxy designates CH 3 OCH2θ; C 3 alkoxyalkoxy designates, for example, CH3OCH2CH2O or CH3CH2OCH2O; and C4 alkoxyalkoxy designates the various isomers of an alkoxy group substituted with a second alkoxy group containing a total of 4 carbon atoms, examples including CH 3 CH 2 CH 2 OCH 2 O, and CH 3 CH 2 OCH 2 CH 2 O. Examples of "alkoxyalkyl" include CH 3 OCH 2 , CH 3 OCH 2 CH 2 , CH 3 CH 2 OCH 2 , CH 3 CH 2 CH 2 CH2OCH2 and CH 3 CH 2 OCH 2 CH 2 . Preferred for reasons of ease of synthesis or greater fungicidal activity are: Preferred 1. The compounds of Formula I as defined above wherein: Q is O; R 1 is C 3 -C 8 alkyl; C 4 -C 8 alkenyl; C 4 -C 8 alkynyl; C r C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 2 -C 8 alkoxyalkyl; C2-C 8 alkylthioalkyl; C5-C cycloalkylalkyl; C2~C alkyl substituted with cyano; Cι-C 8 alkoxy; Cj-C 8 haloalkoxy; C j -C alkylthio; or C4-C 8 alkenyloxyalkyl; or pyridyl, furanyl, or thienyl each optionally substituted with R 14 and R15; R 2 is C 3 -C 8 alkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C r C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 3 -C 8 alkoxyalkyl; C2-C 8 alkylthioalkyl; C4-C 8 cycloalkylalkyl; C -C 8 cyanoalkyl; C4-C 8 alkenyloxyalkyl; or phenyl optionally substituted with R 13 ; R 3 is halogen; C r C 8 alkyl; C 2 -C 8 alkynyl; C 3 -C 8 cycloalkyl; C r C 8 haloalkyl; C C 8 alkoxy; C j -Cg haloalkoxy; C j -Cg alkylthio; C-j-Cg alkylsulfonyl; C2-C 8 alkoxyalkyl; C2~C 8 alkylthioalkyl; C4~C 8 cycloalkylalkyl; or C5-C 8 trialkylsilylalkynyl; and R 14 is methyl; ethyl; methoxy; ethoxy; C1-C2 haloalkyl; halogen; acetylenyl; propargyl; methylthio; ethylthio; cyano; nitro; C1-C2 haloalkoxy; vinyl; allyl; acetyl; CO 2 Me; or N(Cj-C2 alkyl)2. Preferred 2. The compounds of Formula II as defined above wherein: Q is O; nis O; R 3 is halogen; C r C 8 alkyl; C 2 -C 8 alkynyl; C 3 -C 8 cycloalkyl; C r C 8 haloalkyl; Cι-C 8 alkoxy; C j -C haloalkoxy; C^-Cg alkylthio; Cj-C 8 alkylsulfonyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C4-Cg cycloalkylalkyl; or Cs-C trialkylsilylalkynyl; R 5 is C 3 -C 5 alkyl; C4-C7 alkenyl; C 3 -C 5 alkynyl; C r C 8 haloalkyl; C 5 -C 8 haloalkenyl; C 2 -C alkoxyalkyl other than methoxypropyl; C 2 -C alkylthioalkyl; C4-C cycloalkylalkyl; C 2 -Cg alkyl substituted with cyano; C j -Cg alkoxy; C j -Cg haloalkoxy; C^-Cg alkylthio; or C4-C alkenyloxyalkyl; or phenyl, furanyl, or thienyl each optionally substituted with R 14 and R 15 ; R 6 is C 3 -C 8 alkyl; C 3 -C 7 alkenyl; C 3 -C 8 alkynyl; C r C 8 haloalkyl; C 3 -C 8 haloalkenyl; C3-C 8 alkoxyalkyl other than propoxymethyl; C 2 -C alkylthioalkyl; C4-C cycloalkylalkyl; C5~C cyanoalkyl; C4~C 8 alkenyloxyalkyl; phenyl optionally substituted with R 13 ; or C3-C5 alkyl substituted with phenyl optionally substituted with R 13 and R 15 ; and R 14 is methyl; ethyl; methoxy; ethoxy; Cj-C 2 haloalkyl; halogen; acetylenyl; propargyl; methylthio; ethylthio; cyano; nitro; Cj-C 2 haloalkoxy; vinyl; allyl; acetyl; CO 2 Me; or N(Cχ-C2 alkyl) 2 . Preferred 3. The compounds of Formula IQ as defined above wherein: Q is O; R 3 is halogen; C r C 8 alkyl; C 2 -C 8 alkynyl; C 3 -C 8 cycloalkyl; C r C 8 haloalkyl; C j -C 8 alkoxy; Cj-C 8 haloalkoxy; Cι-C 8 alkylthio; Cj-C 8 alkylsulfonyl; C2-C alkoxyalkyl; C2-Cg alkylthioalkyl; C4-Cg cycloalkylalkyl; or C5~C trialkylsilylalkynyl; R 7 is C 3 -Cg alkyl; C4-C7 alkenyl; propynyl; C2-C 8 haloalkyl; C 3 -Cg haloalkenyl; C2-C 8 alkoxyalkyl; C2-Cg alkylthioalkyl; C2-Cg alkyl substituted with cyano; C j -Cg alkoxy; Cj-Cg haloalkoxy; Cj-C alkylthio; or C4~Cg alkenyloxyalkyl; or phenyl, pyridyl, furanyl, or thienyl each optionally substituted with R 14 and R 15 ; R 9 is C 3 -C 8 alkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 3 -C 8 alkoxyalkyl; C2-C 8 alkylthioalkyl; C4-C 8 cycloalkylalkyl; C4-C 8 cyanoalkyl; C4-C alkenyloxyalkyl; -NR 12 R 17 ; or R 3 and R 4 are both iodine and R 9 is phenyl optionally substituted with R 14 and R 15 ; and R 14 is methyl; ethyl; methoxy; ethoxy; C1-C2 haloalkyl; halogen; acetylenyl; propargyl; methylthio; ethylthio; cyano; nitro; C1-C2 haloalkoxy; vinyl; allyl; acetyl; CO2Me; or N(Cj-C2 alkyl)2. Preferred 4. The compounds of Preferreds 1, 2, and 3 wherein: R 1 is C 3 -C 8 alkyl; C 4 -C 8 alkenyl; C 4 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 3 -C 8 alkoxyalkyl; or thienyl optionally substituted with at least one of R 14 and R 15 ; R 2 is C 3 -C 8 alkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 3 -C 8 alkoxyalkyl; or phenyl optionally substituted with R 13 ; R 3 is halogen; C1-C4 alkyl; C1-C4 haloalkyl; C1-C4 alkoxy; C1-C4 haloalkoxy; acetylenyl; or trimethylsilylacetylenyl; R 5 is C 3 -C 5 alkyl; C4-C7 alkenyl; C3-C5 alkynyl; C 3 -C 8 haloalkyl; C 5 -C 8 haloalkenyl; C3~C alkoxyalkyl; or phenyl or thienyl each optionally substituted with R 14 and R 15 ; R 6 is C 3 -C 8 alkyl; C3-C7 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; C3~C 8 alkoxyalkyl; or phenyl optionally substituted with R 13 ; R 7 is C3-C 8 alkyl; C4-C7 alkenyl; propynyl; C3~C haloalkyl; C3-C haloalkenyl; C3-Cg alkoxy; C3-C 8 alkoxyalkyl; or phenyl or thienyl each optionally substituted with R 14 and R 15 ; R 9 is C 3 -C 8 alkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 3 -C 8 alkoxyalkyl; -NR 12 R 17 ; or R 3 and R 4 are both iodine and R 9 is phenyl optionally substituted with R 14 and R 15 ; and R 14 is methyl; ethyl; methoxy; methylthio; halogen; trifluoromethyl; or N(C r C 2 alkyl)2. Preferred 5. The compounds of Preferred 4 wherein: R 1 is C 3 -C 8 alkyl; C 4 -C 8 alkenyl; C 4 -Cg alkynyl; C 3 -C 8 haloalkyl; or C 3 -C 8 haloalkenyl; R 2 is C 3 -C 8 alkyl; C 3 -Cg alkenyl; C 3 -Cg alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; or phenyl optionally substituted with R 13 ; R 3 is halogen; R 4 is hydrogen or halogen; R 5 is C 3 -C 5 alkyl; C 4 -C 7 alkenyl; C 3 -C 5 alkynyl; C 3 -C 8 haloalkyl; or C5~C 8 haloalkenyl; or phenyl optionally substituted with R 14 and Rl* 5 ; R 6 is C 3 -C 8 alkyl; C 3 -C 7 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; or phenyl optionally substituted with R 13 ; R 7 is C 3 -C 8 alkyl; C4-C7 alkenyl; propynyl; C 3 -C haloalkyl; or C 3 -C haloalkenyl; or phenyl optionally substituted with R 14 and R 15 ; and R 9 is C 3 -C 8 alkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; -NR 12 R 17 ; or R 3 and R 4 are both iodine and R 9 is phenyl optionally substituted with R 14 and R 15 . Preferred 6. The compounds of Preferred 5 wherein said compounds are selected from the group: 6-bromo-3-propyl-2-propyloxy-4(3H)-quinazolinone; 6,8-diiodo-3-propyl-2-propyloxy-4(3H)-quinazolinone; 6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone; and 6,8-diiodo-3-propyl-2-(phenylamino)-4(3H)-quinazolinone. It is recognized that some reagents and reaction conditions described below for preparing compounds of Formulae I, π, and IQ may not be compatible with some functionalities claimed for R^R 17 , n, m, and Q. In these cases, the incorporation of protection/deprotection sequences into the synthesis may be necessary in order to obtain the desired products. The cases in which protecting groups are necessary, and which protecting group to use, will be apparent to one skilled in chemical synthesis. See Greene, T. W. and Wuts, P. G. M.; Protective Groups in Organic Synthesis, 2nd Ed.; John Wiley & Sons, Inc.; New York, (1980) for suitable protecting groups. In the following description of the preparation of compounds of Formulae I, π, and HI, compounds of Formulae la and lb, Ha-IIc, and ϋla-IIIe are various subsets of the compounds of Formulae I, π, and HI. All substituents in compounds of Formulae la and lb, ϋa-IIc, and IHa-IIIe and 2-7 are as defined above for Formulae I, π, and El. Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active than the others and how to separate said stereoisomers. Accordingly, the present invention comprises mixtures, individual stereoisomers, and optically active mixtures of compounds of Formulae I, II, and lu as well as agriculturally suitable salts thereof. The compounds of Formulae I, II, and HI can be prepared as described below in Schemes 1-9 and Examples 1-3. Synthesis of Compounds of Formula I Compounds of Formula la, compounds of Formula I wherein Q is O, can be made by the method illustrated in Scheme 1. An anthranilic acid (2-aminobenzoic acid) of Formula 2 is condensed with an isothiocyanate of Formula R^NCS to form the 2-thioquinazolinedione of Formula 3. This condensation is preferably performed in the presence of a base such as triethylamine. 5-Methylation of this compound affords the 2-methylthio-4(3H)-quinazolinone of Formula 4. For the introduction of the R 2 O group, the 2-methylthio-4(3H)-quinazolinone of Formula 4 is treated with a mixture of a base, for example sodium hydride, in R 2 OH solvent. The reaction mixture is stirred at a temperature from about 0°C to 120°C for 1-120 hours. The desired 2-R 2 O-4(3H)-quinazolinone can be isolated from the reaction mixture by extraction into a water-immiscible solvent, and purified by chromatography or recrystallization. Similar synthetic procedures are described in U.S. 3,755,582, incorporated herein by reference. Scheme 1 la Anthranilic acids of Formula 2 are known or can be prepared by known methods. For example see, March, J. Advanced Organic Chemistry; 3rd ed., John Wiley: New York, (1985), p 983. The isothiocyanates of Formula R*-NCS can be prepared from the corresponding amine by treatment with thiophosgene as known in the art. For example, see /. Heterocycl. Chem., (1990), 27, 407. Alternatively, 2-thioquinazolinediones of Formula 3 can be prepared by treatment of the (C1-C4 alkyl) anthranilic acid ester of Formula 5 with thiophosgene to form the isothiocyanate ester, followed by treatment with an amine of formula RiN^ (Scheme 2). Scheme 2 The anthranilic acid ester of Formula 5 is treated with thiophosgene at a temperature from about -20°C to 100°C for 1 to 48 hours optionally in an inert solvent. Often this reaction is performed in a biphasic mixture in the presence of a base, such as calcium carbonate, and an acid, such as aqueous hydrochloric acid. The resulting isothiocyanate may be isolated by extraction into a water-immiscible solvent, such as methylene chloride, followed by drying of the organic extracts and evaporation under reduced pressure. Alternatively, the isothiocyanate can be combined in situ with the amine of Formula H2NR 1 and stirred at about -20°C to 50°C for 0.1 to 24 hours. The desired 2-thioquinazolinediones of Formula 3 can be isolated from the reaction mixture by aqueous extraction, and purified by chromatography or recrystallization. Similar synthetic procedures are described in /. Heterocycl. Chem., (1990), 27, 407. Compounds of Formula lb, compounds of Formula I wherein Q is S, can be prepared as illustrated in Scheme 3. Scheme 3 la lb Treatment of the quinazolinone of Formula la with phosphorous pentasulfide or Lawesson's reagent [2,4-bis(4-methoxyphenyl)-l ,3-dithia-2,4-diphosphetane-2,4- disulfide] in an inert solvent such as dioxane at a temperature from 0°C to the reflux temperature of the solvent for 0.1 to 72 hours affords the quinazolinethione of Formula lb. This procedure is described in the literature, for example see U.S. 3,755,582. Synthesis of Compounds of Formula II 4(3H)-Quinazolinones of Formula Ha, compounds of Formula II wherein n is 0 and Q is O, can be prepared by a modification of the synthesis illustrated in Scheme 1. As illustrated in Scheme 4, the 2-thioquinazolinedione of Formula 6 is alkylated with R 6 -X wherein X is a typical leaving group such as Br, I, CH 3 SO 3 (OMs), or (4-CH3-Ph)SO 3 (OTs) to afford the 2-R 6 S-4(3H)-quinazolinone of Formula Ila. One or more equivalents of a base can be used to accelerate the process. Bases such as sodium hydroxide and sodium hydride are suitable. Scheme 4 X = Br, I, OMs, OTs Ila Typically, the 2-thioquinazolinedione is dissolved or dispersed in an inert solvent such as dimethylformamide and treated with a base at a temperature from about -20°C to 60°C with a base. The reaction mixture may then be heated to just above ambient temperature to the reflux temperature of the solvent for 0.1 to 24 hours to effect deprotonation. After cooling, the reaction mixture is cooled and treated with R 6 -X and stirred for 0.1-24 hours at a temperature from about 20°C to the reflux temperature of the solvent. The quinazolinone of Formula Ha can be isolated by extraction into a water-immiscible solvent, and purified by chromatography or recrystallization. 2-Thioquinazolinediones of Formula 6 are prepared as described above in Schemes 1 and 2 for 2-thioquinazolinediones of Formula 3. 4(3H)-Quinazolinones of Formula lib, compounds of Formula π wherein Q is O and n is 1 or 2, can be prepared by oxidation of the corresponding -SR 6 compound of Formula la using well-known procedures for oxidation of sulfur (Scheme 5). For example, see March, J. Advanced Organic Chemistry; 3rd ed., John Wiley: New York, (1985), p 1089. Scheme 5 4(3H)-Quinazolinethiones of Formula He, compounds of Formula II wherein Q is S, can be prepared by treatment of the corresponding quinazolinone with phosphorous pentasulfide or Lawesson's reagent as described in U.S. 3,755,582 and above for compounds of Formula lb (Scheme 6). Scheme 6 Lawesson's reagent He Synthesis of Compounds of Formula in 4(3H)-Quinazolinones of Formula Ida, compounds of Formula HI wherein Q is O, can be prepared by the method illustrated in Scheme 7. This method is described in detail in U.S. 3,867,384 and incorporated herein by reference. Scheme 7 Z = SMe orα ma 7 One method of preparation of compounds of Formula πia is by treatment of a 2-methylthio-4(3H)-quinazolinone of Formula 7 (Z = SMe) with an excess of an amine of Formula HNR 8 R 9 at about 150°C to 175°C. A second method is to contact a 2-chloro-4(3H)-quinazolinone of Formula 7 (Z = Cl) with one equivalent of HNR 8 R 9 and one equivalent of an acid scavenger, for example triethylamine, or with two equivalents of HNR 8 R 9 , at a temperature between 60°C and 120°C optionally in the presence of a solvent. The preparation of compounds of Formula 7 wherein Z is SMe is described above and in U.S. 3,755,582. The synthesis of compounds of Formula 7 wherein Z is Cl is described in U.S. 3,867,384. Amines of Formula HNR 8 R 9 are commercially available or can be prepared by well-known methods (March, J. Advanced Organic Chemistry; 3rd ed., John Wiley: New York, (1985), p 1153). In addition to the methods described above, compounds of Formula la and Ila can be prepared by displacement of the 2-chlorine in the appropriate 4(3H)-quinazolinone, rather than by displacement of the 2-SCH3 group (Scheme 1) or S-alkylation of the thiocarbonyl (Scheme 4). As described above for compounds of Formula lb and lie, quinazolinethiones of Formula Hlb can be prepared by treatment of the corresponding quinazolinone with P2S5 or Lawesson's reagent (Scheme 8). Scheme 8 Hlb Alternatively, 4(3H)-quinazolinones and quinazolinethiones of Formulae Hid and Hie, compounds of Formula HI wherein R 8 = -C(=O)R 12 , can be prepared by acylation of the corresponding quinazolinones or quinazolinethione wherein R 8 = H (Formula Hie) as illustrated in Scheme 9. Scheme 9 The quinazolinones of Formula Hie can be treated with an acylating agent of Formula R 10 C(=O)L wherein L is an appropriate leaving group such as chlorine or OC(=O)(H or C1-C4 alkyl). In a similar fashion, compounds of Formula HI wherein R 8 is -C(=O)NHR 12 (Formula Hie) can be prepared by condensing quinazolinones of Formula HIc with isocyanates of Formula R 14 N=C=O using well known procedures. Salts of compounds of Formulae I, H, and IE can be formed by treating the free base of the corresponding compound with strong acids such as hydrochloric or sulfuric acid. Salts can also be prepared by alkylation of a tertiary amine group in the molecule to form, for example, the trialkylammonium salt. N-Oxides of compounds of Formulae I, H, and HI can be made by oxidizing the corresponding reduced nitrogen compound with a strong oxidizing agent such as meta-chloroperoxybenzoic acid. EXAMPLE 1 Synthesis of 6-Bromo-3-propyl-2-propyloxy-4(3H)-quinazolinone All reactions were conducted under a nitrogen atmosphere. Step A To a solution of 200 mL of ethanol containing 37 g of 2-amino-5-bromobenzoic acid was added dropwise 17.72 mL of n-propyl isothiocyanate with stirring. The mixture was heated at reflux for 8 h, allowed to cool to room temperature and stirred for approximately 60 h. The mixture was then cooled to approximately 5°C and filtered to obtain 15.42 g of an off-white solid. Step B To a solution containing 15.4 g of the product of Step A dissolved in 100 mL of 10% propanolic sodium hydroxide was added 3.2 mL of iodomethane with stirring. The mixture was stirred at room temperature for 10 min, then heated at reflux for 1.5 h, and then allowed to cool to room temperature and stirred overnight. The reaction mixture was filtered to obtain 11.47 g of a white solid. The white solid was purified by column chromatography on silica gel eluting with hexane and then 9:1 hexane:ethyl acetate. Collection and evaporation of those fractions containing the least polar component (according to thin layer chromatography, 6: 1 hexane/ethyl acetate mixture as the development solvent) yielded 6.55 g of a white solid, m.p. 97-99°C. Step C To 150 mL of propanol cooled to approximately -60°C was added 0.83 g of ΝaH (60% active in oil) with stirring. To this mixture at -60°C was added 6.5 g of the purified product obtained in Step B. The mixture was allowed to warm to room temperature and stirred for approximately 48 h to yield a clear solution. The reaction solution was poured into water and extracted twice with diethyl ether. The ether extracts were washed twice with water, dried over magnesium sulfate, filtered and the filtrate was then evaporated to yield 10.3 g of an oil. Thin layer chromatography indicated starting material and desired product were both present. Step D To propanol cooled to -50°C was added 0.60 g of NaH (60% active in oil) with stirring. To this mixture at -40°C was added the product of Step C and the mixture was allowed to warm to room temperature and stirred for approximately 72 h. The mixture was then heated at reflux for 30 min, cooled to room temperature, poured into water and extracted twice with diethyl ether. The combined ether extracts were washed three times with water, dried over magnesium sulfate, filtered and the filtrate was evaporated to yield an oil. The oil was purified by column chromatography on silica gel eluting with hexane followed by 9:1 hexane/ethyl acetate. Collection and evaporation of the fractions containing only the least polar component (according to thin layer chromatography on silica gel, 9: 1 hexane/ethyl acetate mixture as the development solvent) yielded 4.46 g of the title compound as a white solid, m.p. 57-59°C: -U NMR (400 MHz, CDC1 3 ) δ 8.3 (s,lH), 7.7 (m,lH), 7.3 (m,lH), 4.43 (t,2H), 4.05 (t,2H), 1.85 (m,2H), 1.7 (m,2H), 1.06 (t,3H), 0.97 (t,3H). EXAMPLE 2 Synthesis of 6-Bromo-3-n-butyl-2-n-propylamino-4(3H)-quinazolinone Step A To a solution of 200 mL of ethanol containing 15.15 g of 2-amino-5-bromobenzoic acid was added dropwise 9.3 mL of n-butyl isothiocyanate with stirring. To this reaction solution was added 9.77 mL of triethylamine. The reaction solution was heated at reflux for 4 h during which time a solid precipitated. The reaction mixture was cooled to 0°C and filtered to obtain 19.89 g of an off-white solid, m.p. 246-248°C. Step B To a solution containing 7 g of the product of Step A suspended in 50 mL of chloroform was added 1.97 mL of sulfuryl chloride with stirring. The solution was heated at reflux for 5 h, then cooled to room temperature. The reaction solution was poured into water and extracted twice with methylene chloride. The organic extracts were dried over magnesium sulfate, filtered and the filtrate was then evaporated to a yellow solid. The solid was purified by column chromatography on silica gel eluting with 6: 1 hexane/ethyl acetate. Collection and evaporation of the fractions containing only the second-least polar component (according to thin layer chromatography on silica gel, 4:1 hexane/ethyl acetate mixture as the development solvent) yielded 3.2 g of white solid, m.p. 56-58°C. Step C To a solution containing 1.02 g of the purified product obtained in Step B dissolved in 25 mL of tetrahydrofuran was added 0.5 mL of n-propylamine. The reaction mixture was stirred for approximately 24 h at room temperature. The reaction was then filtered and the filtrate was evaporated to obtain an oil. The oil was dissolved in diethyl ether and washed twice with water and once with brine. The ether solution was dried over magnesium sulfate, filtered and the filtrate was then evaporated to yield 0.74 g of the title compound as a white solid, m.p. 71-73°C: l U NMR (400 MHz, CDC1 3 ) 0.97-1.04 (m,6H), 1.45 (m,2H), 1.70 (m,4H), 3.50 (m,2H), 4.00 (t,2H), 4.50 (s,lH), 7.24 (d,lH), 7.60 (d,lH), 8.20 (s,lH). EXAMPLE 3 Synthesis of 6-Bromo-3-/.-propyl-2-n-propylthio-4(3H)-quinazolinone Step A To a solution of 150 mL isopropanol containing 29.7 g of 2-amino-5- bromobenzoic acid was added dropwise 15.64 mL of n-propyl isothiocyanate with stirring. The reaction mixture was then heated at reflux for 15 h. The reaction mixture was cooled to 0°C and filtered to obtain 9.12 g of an off-white solid. Step B To a solution containing 0.34 g of the product of Step A suspended in 20 mL of 10% propanolic sodium hydroxide was added 0.22 mL of iodopropane with stirring. The reaction mixture was stirred 1.5 h at room temperature. The reaction was poured into water and extracted twice with methylene chloride. The methylene chloride extractions were washed twice with water, dried over magnesium sulfate, filtered, and the filtrate was then evaporated to yield a white solid. The solid was purified by column chromatography on silica gel eluting with 8:1 hexane/ethyl acetate. Collections and evaporation of the fractions containing only the least-polar component (according to thin layer chromatography on silica gel, 6:1 hexane/ethyl acetate mixture as the development solvent) yielded 0.27 g of the title compound as a white solid, m.p. 65-67°C: *H NMR (400 MHz, CDC1 3 ): δ 0.99-1.10 (m,6H), 1.80 (m,4H), 3.25 (t,2H), 4.10 (t,2H), 7.41 (d,lH), 7.78 (d,lH), 8.30 (s,lH). Using the procedures outlined in Schemes 1-9 and Examples 1-3, the compounds of Tables 1-12 hereinafter can be prepared. The compounds referred to in the Tables which follow are illustrated below: The following abbreviations are used in the Tables which follow. All alkyl groups are the normal isomers unless indicated otherwise. See structures in Index Tables A-C hereinafter for ring system numbering. t = tertiary MeO = methoxy s = secondary Pr = propyl n = normal CN = cyano i = iso c = cyclo Me = methyl MeS = methylthio Et = ethyl Bu = butyl Ph = phenyl TABLE 1 Compounds of Formula I wherein: Q = O, R 2 = n* Pr, R 3 = 6-1, R 4 = 8-1, and E 1 R 1 E 1 R 1 n-Pr n-Bu n-pentyl n-hexyl n-decyl i-Pr i-Bu s-Bu c-propyl c-butyl c-pentyl 2-butenyl 3-butenyl 2-butynyl 3-butynyl CF 3 2-Cl-Et 3-Br-Pr CH 2 CH=CHα CH 2 c≡cα CH2 OCH 3 CH 2 OCH 2 CH 3 CH 2 SCH 3 CH 2 SCH 2 CH 3 CH 2 CH 2 SCH 3 CH2CH 2 S(0)CH 3 ( Η 2 C H 2 CH 2 S ( 0 )2 CH 3 (c-pentyl)CH 2 CH2CH 2 OCH 2 CH=CH2 CH2CH2θCH 2 C≡CH (c-hexyl)OCH 2 (c-pentyl)SCH 2 CH2CH2SCH2 CH= C H 2 CH2CH2SCH 2 CsCH CH2OCF3 CH 2 OCH 2 CH 2 α CH 2 OCH 2 CH=CHα CH 2 OCH2C≡CBr CH 2 CH=CHCH 2 OCH 3 CH 2 OCCH 2 OCH 3 CH 2 CH=CHCH 2 SCH 3 CH2C≡CCH 2 SCH 3 CH 2 CH 2 Si(CH 3 ) 3 CH 2 CH 2 N(CH 3 ) 2 CH 2 CH 2 CH 2 NHCH 3 CH2CH2NO2 CH 2 CH 2 CH 2 CN PhCH 2 OCH 2 CH 2 CH 3 OCH 2 CH2CF 3 SCH 2 CH 3 scα 3 SCH 2 CH 2 α NHCH2CH 2 CH 3 N(CH 3 )CH 2 CH 3 (2-Me-Ph)CH 2 CH 2 2-pyridinyl 2-furanyl 2-thienyl 2-naphthyl 5-benzofuranyl 3-benzothienyl 3-quinolinyl (4-F-Ph)CH 2 TABLE 2 Compounds of Formula I wherein: Q = 0, R 1 *** : n-Pr, R 3 = 6-Br, R 4 = H, and B 2 S 2 R 2 E 2 CH 2 CH 2 CH 2 F t-Bu i-Pr n-Bu i-Bu s-Bu n-pentyl n-hexyl n-decyl c-hexyl allyl 2-butenyl 3-butenyl 5-decenyl propargyl 2-butynyl 3-butynyl CF 3 CH 2 CF 3 CH 2 CH=CHC1 CH 2 C≡CBr CH 2 OCH 3 CH 2 OCH 2 CH 3 CH 2 CH2θCH 3 CH 2 SCH 3 CH 2 CH2SCH 3 CH 2 CH2CH2S(0)2CH3 (c-pentyl)CH 2 2-α-Et CH 2 CH 2 OCH 2 C≡CH GH2CH 2 SCH2 CH:= H 2 (c-propyl)OCH 2 (c-hexyl)SCH 2 CH2CH 2 OCF 3 (^2 <:Ή 2 SCH 2 CSCH CH2CH2CH2CN CH 2 CH2Si(CH 3 ) 3 -NHPh CH2OCH2CH2CI CH 2 (4-F-Ph) -N(CH 3 )Ph CH 2 CH2CH2N(CH 3 )2 CH 2 CH2CH2Ph CH 2 CH 2 CH 2 F CH 2 Ph CΗ 2 CH2 0CH 2 CH = H 2 CH 2 CH2Ph CH 2 CH2CH2NHCH 3 CH 2 CH 2 N0 2 -N=CHPh GH 2 CH2(4-F-Ph) -N=CHCH 2 CH 2 CH 3 -N=C(CH 3 ) 2 NHCH 2 CH 2 CH 3 Ν(CH 3 ) 2 TABLE 3 Compounds of Formula II wherein: Q = O, n is 0, R° = n-Pr, R 3 = 6-Br, R 4 = H, and E 5 E 5 E 5 E 5 n-Pr n-Bu n-pentyl n-octyl TABLE TABLE 7 Compounds of Formula III wherein: Q = O, R 8 = H, R 9 = n-Pr, R 3 = 6-Br, R 4 = H, and R 7 E 7 E 7 E 7 n-Pr n-Bu n-pentyl n-hexyl c-hexyl i-Pr i-Bu s-Bu TABLE 11 Compounds of Formula III wherein Q = O, Compounds of Formula III wherein Q = O, R8 = C(=0)OCH 3 R 8 = C(=0)CH 3 E 7 E 9 E 3 E 4 E 7 E 9 B 3 B 4 n-Pr n-Pr 6-Br H n-Pr n-Pr 6-Br H Compounds of this invention will generally be used in formulation with an agriculturally suitable composition. The fimgicidal compositions of the present invention comprise an effective amount of at least one compound of Formula I, π, or in as defined above and at least one of (a) a surfactant, (b) an organic solvent, and (c) at least one solid or liquid diluent. Useful formulations can be prepared in conventional ways. They include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, dry flowables and the like. Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up 100 weight percent. Weight Percent High Strength Compositions 90-99 0-10 0-2 Typical sohd diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey. Typical liquid diluents and solvents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, (1950). McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, New Jersey, as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, (1964), list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, and the like. Methods for formulating such compositions are well known. Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer mill or fluid energy mill. Water-dispersible granules can be produced by agglomerating a fine powder composition; see for example, Cross et al., Pesticide Formulations, Washington, D.C., (1988), pp 251-259. Suspensions are prepared by wet-milling; see, for example, U.S. 3,060,084. Granules and pellets can be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration", Chemical Engineering, December 4, 1967, pp 147-148, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, (1963), pp 8"57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in DE 3,246,493. For further information regarding the art of formulation, see U.S. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10 through 41; U.S. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, (1961), pp 81-96; and Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, (1989). In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound 1 refers to the compound described in Index Table A hereinafter. Example A Wettable Powder Compound 1 65.0% dodecylphenol polyethylene glycol ether 2.0% sodium ligninsulfonate 4.0% sodium silicoaluminate 6.0% montmorillonite (calcined) 23.0%. Example B Granule Compound 37 10.0% attapulgite granules (low volative matter, 0.71/0.30 mm; U.S.S. No. 25-50 sieves) 90.0%. Example C Extruded Pellet Compound 25 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate 5.0% sodium alkylnaphthalenesulfonate 1.0% calcium/magnesium bentonite 59.0%. Example D Emulsifiable Concentrate Compound 37 20.0% blend of oil soluble sulfonates and polyoxyethylene ethers 10.0% isophorone 70.0%. The compounds of this invention are useful as plant disease control agents, especially for the control of cereal powdery mildews (e.g., Erysiphe graminisf. sp. tritici, the causal agent of wheat powdery mildew). The present invention therefore further comprises a method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof to be protected, or to the plant seed or seedling to be protected, an effective amount of a compound of Formula I, π, or IE or a fungicidal composition containing said compound. The compounds and compositions of this invention provide control of diseases caused by a broad spectrum of fungal plant pathogens in the Basidiomycete, Ascomycete, Oomycete and Deuteromycete classes. They are effective in controlling a broad spectrum of plant diseases, particularly fohar pathogens of ornamental, vegetable, field, cereal, and fruit crops. These pathogens include Plasmopara viticola, Phytophthora infestans, Peronospora tabacina, Pseudoperonospora cubensis, Pythium aphanidermatum, Alterriaria brassicae, Septoria nodorum, Cercosporidium personatum, Cercospora arachidicola, Pseudocercosporella herpotrichoides, Cercospora beticola, Botrytis cinerea, Monilinia fructicola, Pyricularia oryzae, Podosphaera leucotricha, Venturia inaequalis, Erysiphe graminis, Uncinula necatur, Puccinia recondita, Puccinia graminis, Hemileia vastatrix, Puccinia striiformis, Puccinia arachidis, Rhizoctonia solani, Sphaerotheca fuliginea, Fusarium oxysporum, Verticillium dahliae, Pythium aphanidermatum, Phytophthora megasperma and other generea and species closely related to these pathogens. Compounds of this invention can also be mixed with one or more other insecticides, fungicides, nematocides, bactericides, acaricides, semiochemicals, repellants, attractants, pheromones, feeding stimulants or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of agricultural protection. Examples of other agricultural protectants with which compounds of this invention can be formulated are: insecticides such as acephate, avermectin B, azinphosmethyl, bifenthrin, biphenate, buprofezin, carbofuran, chlordimeform, chloφyrifos, cyfluthrin, deltamethrin, diazinon, diflubenzuron, dimethoate, esfenvalerate, fenpropathrin, fenvalerate, fipronil, flucythrinate, flufenprox, fluvalinate, fonophos, isofenphos, malathion, metaldehyde, metha-midophos, methidathion, methomyl, methoprene, methoxychlor, monocrotophos, oxamyl, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, rotenone, sulprofos, terbufos, tetrachlorvinphos, thiodicarb, tralomethrin, trichlorfon and triflumuron; fungicides such as benomyl, blasticidin S, bromuconazole, captafol, captan, carbendazim, chloroneb, chlorothalonil, copper oxychloride, copper salts, cymoxanil, cyproconazole, cyrodinil, dichloran, diclobutrazol, diclomezine, difenoconazole, diniconazole, dodine, edifenphos, epoxyconazole fenarimol, fenbuconazole, fenpropidine, fenpropimoφh, fluquinconazole, flusilazol, flutolanil, flutriafol, folpet, furalaxyl, hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamycin, mancozeb, maneb, mepronil, metalaxyl, metconazole, myclobutanil, neo-asozin, oxadixyl, penconazole, pencycuron, phosethyl-Al, probenazole, prochloraz, propiconazole, pyrifenox, pyrimethanil, pyroquilon, sulfur, tebuconazole, tetraconazole, thiabendazole, thiophanate-methyl, thiuram, triadimefon, triadimenol, tricyclazole, triticonazole, uniconzole, validamycin and vinclozolin; nematocides such as aldoxycarb, fenamiphos and fosthietan; bactericides such as oxytetracyline, streptomycin and tribasic copper sulfate; acaricides such as amitraz, binapacryl, chlorobenzilate, cyhexatin, dicofol, dienochlor, fenbutatin oxide, hexythiazox, oxythioquinox, propargite and tebufenpyrad; and biological agents such as Bacillus thuringiensis and baculovirus. In certain instances, combinations with other fungicides having a similiar spectrum of control but a different mode of action will be particularly advantageous for resistance management. Preferred combinations comprise a compound of Formula I, U, or HI, and a fungicide selected from the group flusilazole, cyproconazole, tetraconazole, fenpropimoφh, fenpropidine, cymoxanil, benomyl, carbendazim, mancozeb, and maneb. Plant disease control is ordinarily accomplished by applying an effective amount of a compound of this invention either pre- or post-infection, to the portion of the plant to be protected such as the roots, stems, foliage, fruit, seeds, tubers or bulbs, or to the media (soil or sand) in which the plants to be protected are growing. The compounds can also be applied to the seed to protect the seed and seedling. Rates of application for these compounds can be influenced by many factors of the environment and should be determined under actual use conditions. Foliage can normally be protected when treated at a rate of from less than 1 g/ha to 5,000 g/ha of active ingredient. Seed and seedlings can normally be protected when seed is treated at a rate of from 0.1 to 10 g per kilogram of seed. The following TESTS demonstrate the control efficacy of compounds of this invention on specific pathogens. The pathogen control protection afforded by the compounds is not limited, however, to these species. See Index Tables A, B, and C for compound descriptions. Test compounds were first dissolved in acetone in an amount equal to 3% of the final volume and then suspended at a concentration of 200 ppm in purified water containing 250 ppm of the surfactant Trem® 014 (polyhydric alcohol esters). The resulting test suspensions were then used in the following tests. TEST A The test suspension was sprayed to the point of run-off on wheat seedlings. The following day the seedlings were inoculated with a spore dust of Erysiphe graminis f sp. tritici, (the causal agent of wheat powdery mildew) and incubated in a growth chamber at 20°C for 7 days, after which disease ratings were made. TEST B The test suspension was sprayed to the point of run-off on wheat seedlings. The following day the seedlings were inoculated with a spore suspension of Puccinia recondita (the causal agent of wheat leaf rust) and incubated in a saturated atmosphere at 20°C for 24 h, and then moved to a growth chamber at 20°C for 6 days, after which disease ratings were made. TEST C The test suspension was sprayed to the point of run-off on tomato seedlings. The following day the seedlings were inoculated with a spore suspension of Phytophthora infestans (the causal agent of potato and tomato late blight) and incubated in a saturated atmosphere at 20°C for 24 h, and then moved to a growth chamber at 20°C for 5 days, after which disease ratings were made. TEST D The test suspension was sprayed to the point of run-off on grape seedlings. The following day the seedlings were inoculated with a spore suspension of Plasmopara viticola (the causal agent of grape downy mildew) and incubated in a saturated atmosphere at 20°C for 24 h, moved to a growth chamber at 20°C for 6 days,and then incubated in a saturated atmosphere at 20°C for 24 h, after which disease ratings were made. TEST E The test suspension was sprayed to the point of run-off on cucumber seedlings. The following day the seedlings were inoculated with a spore suspension of Botrytis cinerea (the causal agent of gray mold on many crops) and incubated in a saturated atmosphere at 20°C for 48 h, and moved to a growth chamber at 20°C for 5 days, after which disease ratings were made. 10 In the Tables below, a = -tø NMR data for oils are listed in Index Table D Index Table A la Compounds of Formula la: Index Table B πa Compounds of Formula Ha: CmpdNo. R 5 R 6 R 3 R 4 m.p. (°C) 60 CH 2 CH 2 CH 3 CH 2 CH 2 CH 3 6-1 H 90-92 61 CH 2 CH 2 CH 3 CH 2 CH 2 CH 3 6-Br H 65-67 Index Table C ma 77 CH 2 CH 2 CH 3 CH 2 CH=CH2 H 6-Br H 104-106 79 CH2CH 2 CH 3 CH 2 CH2CH=CH2 H 6-Br H 72-75 80 CH2CH 2 CH 3 Ph H 6-1 8-1 159-162 Index Table D Cmpd No. *H NMR Data b 5 7.46 (dd,lH), 7.29 (d,lH), 7.04 (d,lH), 4.42 (t,2H), 4.02 (m,2H), 2.84 (s,3H), 1.85 (m,2H), 1.71 (m,2H), 1.06 (t,3H), 0.98 (t,3H). 8 8.17 (dd,lH), 7.09 (dd,lH), 7.00 (dt,lH), 4.43 (t,2H), 4.05 (m,2H), 1.85 (m,2H), 1.73 (m,2H), 1.07 (t,3H), 0.97 (t,3H). 27 0.93-0.99 (2-t,6H), 1.37 (m,4H), 1.48 (m,2H), 1.75 (m,2H), 1.80 (m,2H), 4.05 (t,2H), 4.46 (t,2H), 7.34 (d,lH), 7.70 (d,lH), 8.30 ( B). 30 0.94-0.98 (t,3H), 1.70 (m,2H), 2.59 (m,2H), 4.02 (t,2H), 4.53 (t,2H), 5.19 (dd,2H), 5.90 (m,lH), 7.40 (d,lH), 7.59 (d,lH), 8.12 (s,lH). 33 0.93-0.98 (t,3H), 1.70 (m,2H), 2.60 (q,2H), 4.03 (t,2H), 4.51-4.55 (t,2H), 5.20 (dd,2H), 8.29, 8.30 (m,lH). 34 0.95-0.99 (m,6H), 1.41 (m,4H), 1.70 (m,2H), 1.81 (m,2H), 4.05 (t,2H), 4.44-4.48 (t,2H), 7.40 (d,lH), 7.58 (d,lH), 8.13 (s,lH). 38 0.94-1.03 (2-t,6H), 1.40 (m,2H), 1.48 (m,2H), 1.65 (m,2H), 1.80 (m,2H), 4.10 (t,2H), 4.47 (t,2H), 7.34 (d,lH), 7.70 (d,lH), 8.29 (s,lH). 43 2.22 (s,6H), 7.33 (d,lH), 7.71 (d,lH), 8.30 (s,lH). 47 1.45 (d,3H), 7.30 (d,lH), 7.68 (d,lH), 8.29 (s,lH). 48 7.31 (d,lH), 7.69 (d,lH), 8.30 (s,lH). 63 0.88-0.92 (m,9H), 1.59 (m,4H), 1.75 (m,2H), 3.09-3.13 (t,4H), 4.08 (t,2H), 7.38 (d,lH), 7.70 (d,lH), 8.30 (s,lH). 70 0.99 (m,6H), 1.44 (m,4H), 1.66 (m,2H), 3.53 (q,2H), 4.00 (t,2H), 4.49 (s,lH), 7.25 (d,lH), 7.61 (d,lH), 8.10 (s,lH). 72 8.40 (s,lH), 7.89 (d,lH), 7.10 (d,lH), 4.50 (s,lH), 4.0 (t,2H), 3.53 (q,2H), 1.68 (m,4H), 1.45 (m,4H), 0.96-1.01 (m,6H). 73 8.40 (s,lH), 7.79 (d,lH), 7.10 (d,lH), 4.52 (s,lH), 4.0 (t,2H), 3.49 (q,2H), 1.70 (m,4H), 1.43 (m,2H), 0.96-1.02 (m,6H). b Unless indicated otherwise, -H NMR spectra were obtained in CDC1 3 on a 400 MHz spectrometer. Data are reported in ppm downfield from tetramethylsilane; s = singlet, d = doublet, t = triplet, m = multiplet, dd = doublet of doublets, dt = doublet of triplets. Results for Tests A-E are given in Table 13. In the table, a rating of 100 indicates 100% disease control and a rating of 0 indicates no disease control (relative to the controls). "-" = not tested. Table 13 Test Test Test Test Test Test was run at 10 ppm unless otherwise indicated. Test was run at 40 ppm. Test was run at 2 ppm.

Claims: CLAIMS 1. A compound of Formula I, II, or in wherein: n is 0, 1 or 2; Q is independently O or S; R 1 is C3-C 0 alkyl; C3-C 5 cycloalkyl; C -CJO alkenyl; C 4 -CI Q alkynyl; Cι-C -1 l 0 υ haloalkyl; C 3 -C J Q haloalkenyl; C3-C10 haloalkynyl; C2-C10 alkoxyalkyl; C2-C10 alkylthioalkyl; C2-C1Q alkylsulfinylalkyl; C2-C10 alkylsulfonylalkyl; C5-C10 cycloalkylalkyl; C 4 -Cιo alkenyloxyalkyl; C -CJO alkynyloxyalkyl; 4 -C 1 0 (cycloalkyl)oxyalkyl; C 4 -CJO alkenylthioalkyl; C 4 -CJO alkynylthioalkyl; Cg-C^o (cycloalkyl)thioalkyl; C2-C10 haloalkoxyalkyl; C 4 -Cιø haloalkenyloxyalkyl; C 4 -C j ø haloalkynyloxyalkyl; C 4 -Cιo alkoxyalkenyl; C 4 -CI Q alkoxyalkynyl; C 4 -CI Q alkylthioalkenyl; C -C 1 j 0ø alkylthioalkynyl; C -CI Q trialkylsilylalkyl; Cj-Cio alkyl substimted with I NR 1:l R 12 , nitro, cyano, or phenyl optionally substimted with R 14 , R 15 , a t_n-.«d_ R 16 ; C r C 10 alkoxy; C r C 10 haloalkoxy; C^C^ alkylthio; C r C 10 haloalkylthio; NR-^R 12 ; or pyridyl, furanyl, thienyl, naphthyl, benzofuranyl, benzothienyl, or quinolinyl each optionally substimted with R 14 , R 15 , and Rl6 ; R 2 is C3-C10 alkyl; Cg-C 7 cycloalkyl; C3-C10 alkenyl; C3-C10 alkynyl; haloalkyl; C3-C10 haloalkenyl; C3-C10 haloalkynyl; C2-C10 alkoxyalkyl; C2-C1 Q alkylthioalkyl; C2-C1 Q alkylsulfinylalkyl; C2-C10 a__kylsulfonyla_kyl; C4-C10 cycloalkylalkyl; C 4 -CJO alkenyloxyalkyl; C -Cιo alkynyloxyalkyl; C4-C10 (cycloalkyl)oxyalkyl; C 4 -CI Q alkenylthioalkyl; C -CJO alkynylthioalkyl; Cg-C^o (cycloalkyl)thioalkyl; C2-C10 haloalkoxyalkyl; C 4 -C10 haloalkenyloxyalkyl; C 4 -CJO haloalkynyloxyalkyl; C 4 -Cιø alkoxyalkenyl; C 4 -CIQ alkoxyalkynyl; C 4 -CIQ alkylthioalkenyl; C -CIQ alkylthioalkynyl; C -C j ø trialkylsilylalkyl; C3-C10 cyanoalkyl; C2-C10 nitroalkyl; C r C 10 alkyl substituted with CO 2 R π , NR-UR 12 , or phenyl optionally substimted with R 13 , R 15 , and R 16 ; phenyl optionally substituted with R 13 , R 15 , and R 16 ; -N^RHR 11 ; or -NR^R 12 ; or R 1 and R 2 are taken together to form -CH 2 (CH 2 ) m CH2-; m is 1-4 * R 3 is halogen; Cι~C alkyl; C 3 -C 8 cycloalkyl; C2-C 8 alkenyl; C2-Cg alkynyl; Cj-Cg haloalkyl; C 3 -Cg haloalkenyl; C 3 -Cg haloalkynyl; C j -Cg alkoxy; Cj-C haloalkoxy; C 3 -Cg alkenyloxy; C -Cg alkynyloxy; C j -Cg alkylthio; C 3 -Cg alkenylthio; C 3 -C 8 alkynylthio; C j -Cg alkylsulfinyl; C j -Cg alkylsulfonyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C 2 -C 8 alkylsulfinylalkyl; C -C 8 alkylsulfonylalkyl; C 4 -C 8 cycloalkylalkyl; C 3 -C 8 trialkylsilyl; nitro; NR 1 -R 12 ; C 5 -C trialkylsilylalkynyl; or phenyl optionally substituted with at least one RI 3 ; R 4 is hydrogen; halogen; C j -C 4 alkyl; C r C 4 haloalkyl; C1-C4 alkoxy; or C r C 4 haloalkoxy; R 5 is C 3 -C 5 alkyl; C 7 -C 10 alkyl; C 4 -C 7 alkenyl; C 3 -C 5 alkynyl; C r C 10 haloalkyl; C 5 -C!o haloalkenyl; C 3 -CJO haloalkynyl; C2-C10 alkoxyalkyl other than methoxypropyl; C2-C10 alkylthioalkyl; C2-CJ alkylsulfinylalkyl; C2-C 10 alkylsulfonylalkyl; C 4 -CJO cycloalkylalkyl; C 4 -CJO alkenyloxyalkyl; CC4 4 -*C10 alkynyloxyalkyl; C 4 -CI Q (cycloalkyl)oxyalkyl; C -CJO alkenylthioalkyl; C -C 10 alkynylthioalkyl; C 6 -C 10 (cycloalkyl)dιioalkyl; C 2 -C 10 haloalkoxyalkyl; C 4 -CI Q haloalkenyloxyalkyl; C 4 -CJO haloalkynyloxyalkyl; C -CJO alkoxyalkenyl; C 4 -CI Q alkoxyalkynyl; C 4 -CJO alkylthioalkenyl; C -CJO alkylthioalkynyl; C 4 -CI Q trialkylsilylalkyl; CJ-CI Q alkyl substimted with NR 1:l R 12 , nitro, or phenyl optionally substituted with at least one of R 14 , R 15 , and R 16 ; C 2 -C 10 alkyl substimted with cyano; C r C 10 alkoxy; C r C 10 haloalkoxy; C r C 10 alkylthio; haloalkylthio; NR n R 12 ; or phenyl, furanyl, thienyl, naphthyl, benzofuranyl, or benzothienyl each optionally substituted with R 14 , R 15 , and R 16 ; R 6 is C 3 -C 10 alkyl; C 3 -C 7 alkenyl; C 3 -C 10 alkynyl; C r C 10 haloalkyl; C C 3 3- 10 haloalkenyl; C3-C10 haloalkynyl; C3-C1 alkoxyalkyl other than propoxymethyl; C2-C10 alkylthioalkyl; C2-C10 alkylsulfinylalkyl; C2 22-"-MC1io alkylsulfonylalkyl; C 4 -CJO cycloalkylalkyl; C 4 -CI Q alkenyloxyalkyl; C4- 1 10 alkynyloxyalkyl; C 4 -CI Q (cycloalkyl)oxyalkyl; C 4 -C*to alkenylthioalkyl; C 4 -Cχo alkynylthioalkyl; Cg-Cj Q (cycloalkyl)thioalkyl; C2-C10 haloalkoxyalkyl; C 4 -C 1Q haloalkenyloxyalkyl; C 4 -CJO haloalkynyloxyalkyl; C 4 -Cιo alkoxyalkenyl; C -CJO alkoxyalkynyl; C 4 -CJO alkylthioalkenyl; C4-C-K) alkylthioalkynyl; C 4 -CI Q trialkylsilylalkyl; C5-CK) cyanoalkyl; C2-C10 nitroalkyl; or C 3 -C 10 alkyl substimted with CO 2 R π . NR n R 12 , or phenyl optionally substituted with R 13 , R 15 , and R 16 ; or phenyl optionally substimted with R 13 , R 15 , and R 16 ; or R 5 and R 6 are taken together to form -CH 2 (CH 2 ) m CH 2 -; R 7 is C3-C10 al yl; C3-C7 cycloalkyl; C4-C7 alkenyl; propynyl; C5-C10 alkynyl; C 2 -C 10 haloalkyl; C 3 -C 10 haloalkenyl; C 3 -C 10 haloalkynyl; C 2 -C 1( ) alkoxyalkyl; C 2 -Cκ) alkylthioalkyl; C 2 -C j ø alkylsulfinylalkyl; C -CJO alkylsulfonylalkyl; C 4 -CI alkenyloxyalkyl; C 4 -CI Q alkynyloxyalkyl; C 4 -Cjø (cycloalkyl)oxyalkyl; C 4 -C 10 alkenylthioalkyl; C 4 -CI Q alkynylthioalkyl; Cg-Cjo (cycloalkyl)thioalkyl; C 2 -CJO haloalkoxyalkyl; C 4 -CJO haloalkenyloxyalkyl; C 4 -C j g haloalkynyloxyalkyl; C 4 -C j Q alkoxyalkenyl; C -CJO alkoxyalkynyl; C -Cιo alkylthioalkenyl; C 4 -CJO alkylthioalkynyl; C 4 -C 10 trialkylsilylalkyl; C r C 10 alkyl substimted with NR 1 ;l R 12 or nitro; C 2 -CJ Q alkyl substimted with cyano; alkoxy; CJ-CI Q haloalkoxy; Ci-Ciø alkylthio; CJ-CJO haloalkylthio; NR 12 R 17 ; or phenyl, pyridyl, furanyl, thienyl, naphthyl, benzofuranyl, benzothienyl, or quinolinyl each optionally substituted with R 14 , R 15 , and R 16 ; R 8 is hydrogen; C r C 4 alkyl; or -C(=O)R 10 ; R 9 is hydrogen; C 2 -CI Q alkyl; C 3 -C7 cycloalkyl; C 3 -CI Q alkenyl; C 3 -CJO alkynyl; C 3 -CJO haloalkyl; C 3 -CJO haloalkenyl; C 3 -Cιø haloalkynyl; C 3 -C 1Q alkoxyalkyl other than butoxyethyl; C 2 -C Q alkylthioalkyl; C -C 1 Q alkylsulfinylalkyl; C 2 -C 1Q alkylsulfonylalkyl; C 4 -CJO cycloalkylalkyl; C -Cιø alkenyloxyalkyl; C 4 -CJO alkynyloxyalkyl; C4-C10 (cycloalkyl)oxyalkyl; C -Cιo alkenylthioalkyl; C -C 10 alkynylthioalkyl; Cg-Cio (cycloalkylthioalkyl; C 2 -CJO haloalkoxyalkyl; C -CI Q haloalkenyloxyalkyl; C 4 -CJO haloalkynyloxyalkyl; C 4 -CJO alkoxyalkenyl; C4-C10 alkoxyalkynyl; C 4 -Cιo alkylthioalkenyl; C 4 -CJO alkylthioalkynyl; C4-C10 trialkylsilylalkyl; CJ-CJO alkyl substimted with NR U R 12 ; C 4 -C 10 cyanoalkyl; C 2 -C 10 nitroalkyl; Cj-Cg alkyl substimted with CO 2 R 1 :l ; pyridyl, furanyl, thienyl, or naphthyl each optionally substituted with R 14 , R 15 , and R 16 ; -N=CR 11 R 11 ; -NR 12 R 17 ; -OR 12 ; or -NC(=Q)NR 11 R 12 ; or R 3 and R 4 are both iodine and R 9 is phenyl optionally substimted with R 14 , R 15 , and R 16 ; or R 7 and R 9 are taken together to form -CH 2 (CH 2 ) m CH 2 -; R 10 is hydrogen; C r C 4 alkyl; C r C 4 alkoxy; orNR 1 -^ 12 ; R 11 is independently hydrogen; Cj-C 4 alkyl; or phenyl optionally substimted with at least one R 13 ; R 12 is independently hydrogen; Cj-Cg alkyl; or phenyl optionally substituted with at least one R 13 ; or R 11 and R 12 are taken together to form -CH 2 CH 2 CH 2 CH 2 -, -CH 2 (CH 2 ) 3 CH 2 -, -CH 2 CH 2 OCH 2 CH 2 -, -CH 2 CH(Me)CH 2 CH(Me)CH2-, or -CH 2 CH(Me)OCH(Me)CH 2 -; R 13 is independently halogen; C j -C 4 alkyl; C j -C alkoxy; C- ( -C 4 haloalkyl; nitro; or cyano; R 14 is independently C j -Cg alkyl; C j -Cg alkoxy; C r Cg haloalkyl; halogen; C2-Cg alkynyl; Cj-Cg thioalkyl; phenyl or phenoxy each optionally substimted with at least one R 13 ; cyano; nitro; C j -Cg haloalkoxy; C j -Cg haloalkylthio; C2-Cg alkenyl; C2-Cg haloalkenyl; acetyl; CO2Me; or N(Cι-C 2 alkyl) 2 ; R 15 is independently methyl; ethyl; methoxy; methylthio; halogen; or trifluoromethyl; R 16 is independendy halogen; and R 17 is independently C j -Cg alkyl; or phenyl optionally substimted with at least one R 13 ; or an N-oxide or agriculturally-suitable salt thereof. 2. A compound of Formula I of Claim 1 wherein: Q is O; R 1 is C 3 -C 8 alkyl; C 4 -C 8 alkenyl; C 4 -C 8 alkynyl; C r C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 2 -C alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C5~C 8 cycloalkylalkyl; C 2 -C alkyl substimted with cyano; Cj-Cg alkoxy; Cj-Cg haloalkoxy; Cj-Cg alkylthio; or C 4 -Cg alkenyloxyalkyl; or pyridyl, furanyl, or thienyl each optionally substimted with R 14 and R 15 ; R 2 is C 3 -C 8 alkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C r C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 3 -C alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C 4 -C 8 cycloalkylalkyl; C -C 8 cyanoalkyl; C 4 -Cg alkenyloxyalkyl; or phenyl optionally substimted with R 13 ; R 3 is halogen; C j -Cg alkyl; C 2 -C 8 alkynyl; C 3 -Cg cycloalkyl; C j -Cg haloalkyl; C j -Cg alkoxy; C j -Cg haloalkoxy; C j -C 8 alkylthio; Cι-C 8 alkylsulfonyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C 4 -C 8 cycloalkylalkyl; or C 5 -C 8 trialkylsilylalkynyl; and R 14 is methyl; ethyl; methoxy; ethoxy; Cj-C 2 haloalkyl; halogen; acetylenyl; propargyl; methylthio; ethylthio; cyano; nitro; C-(-C 2 haloalkoxy; vinyl; allyl; acetyl; CO 2 Me; or Ν(C r C 2 alkyl) 2 . 3. A compound of Formula H of Claim 1 wherein: Q is O; n is O; R 3 is halogen; C C 8 alkyl; C 2 -C 8 alkynyl; C 3 -C 8 cycloalkyl; C C 8 haloalkyl; C j -Cg alkoxy; C r C 8 haloalkoxy; C r Cg alkylthio; C^Cg alkylsulfonyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C -C 8 cycloalkylalkyl; or C 5 -C 8 trialkylsilylalkynyl; R 5 is C 3 -C 5 alkyl; C 4 -C 7 alkenyl; C 3 -C 5 alkynyl; C r C 8 haloalkyl; C 5 -C 8 haloalkenyl; C 2 -Cg alkoxyalkyl other than methoxypropyl; C 2 -Cg alkylthioalkyl; C 4 -Cg cycloalkylalkyl; C 2 -Cg alkyl substimted with cyano; C j -Cg alkoxy; C r Cg haloalkoxy; C r Cg alkylthio; or C 4 -Cg alkenyloxyalkyl; or phenyl, furanyl, or thienyl each optionally substimted with R 14 and R 15 ; R 6 is C 3 -C 8 alkyl; C 3 -C 7 alkenyl; C 3 -C 8 alkynyl; C r C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 3 -C 8 alkoxyalkyl other than propoxymethyl; C 2 -C 8 alkylthioalkyl; C 4 -C 8 cycloalkylalkyl; C5-C 8 cyanoalkyl; C 4 -C 8 alkenyloxyalkyl; phenyl optionally substituted with R 13 ; or C3-C5 alkyl substimted with phenyl optionally substimted with R 13 and R 15 ; and R 14 is methyl; ethyl; methoxy; ethoxy; Cι-C 2 haloalkyl; halogen; acetylenyl; propargyl; methylthio; ethylthio; cyano; nitro; Cι-C 2 haloalkoxy; vinyl; allyl; acetyl; CO 2 Me; or N(C r C 2 alkyl) 2 . 4. A compound of Formula HI of Claim 1 wherein: Q is O; R 3 is halogen; C r Cg alkyl; C 2 -Cg alkynyl; C 3 -Cg cycloalkyl; Cj-Cg haloalkyl; C- f Cg alkoxy; C j -Cg haloalkoxy; Cχ-Cg alkylthio; Cχ-Cg alkylsulfonyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C -C cycloalkylalkyl; or C5-C 8 trialkylsilylalkynyl; R 7 is C3-C alkyl; C 4 -C7 alkenyl; propynyl; C 2 -C haloalkyl; C3~C haloalkenyl; C 2 -C 8 alkoxyalkyl; C 2 -C alkylthioalkyl; C 2 -C 8 alkyl substimted with cyano; C^Cg alkoxy; Cj-Cg haloalkoxy; Cj-Cg alkylthio; or C 4 -Cg alkenyloxyalkyl; or phenyl, pyridyl, furanyl, or thienyl each optionally substimted with R 14 and R 15 ; R 9 is C 3 -C 8 alkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; C3-C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C 4 -C 8 cycloalkylalkyl; C 4 -C 8 cyanoalkyl; C 4 -C 8 alkenyloxyalkyl; -NR 12 R 17 ; or R 3 and R 4 are both iodine and R 9 is phenyl optionally substimted with R 14 and R 15 ; and R 14 is methyl; ethyl; methoxy; ethoxy; Cj-C 2 haloalkyl; halogen; acetylenyl; propargyl; methylthio; ethylthio; cyano; nitro; Cι-C 2 haloalkoxy; vinyl; allyl; acetyl; CO 2 Me; or N(C r C 2 alkyl) 2 . 5. A compound of Claim 2 wherein: R 1 is C 3 -C 8 alkyl; C 4 -C 8 alkenyl; C 4 -Cg alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 3 -C alkoxyalkyl; or thienyl optionally substituted with at least one of R 14 and R 15 ; R 2 is C 3 -C 8 alkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 3 -Cg alkoxyalkyl; or phenyl optionally substimted withR 13 ; R 3 is halogen; Cj-C 4 alkyl; C r C 4 haloalkyl; C j -C 4 alkoxy; C j -C haloalkoxy; acetylenyl; or trimethylsilylacetylenyl; and R 14 is methyl; ethyl; methoxy; methylthio; halogen; trifluoromethyl; or N(C r C 2 alkyl) 2 . 6. A compound of Claim 3 wherein: R 3 is halogen; Cj-C 4 alkyl; C r C 4 haloalkyl; C j -C 4 alkoxy; C r C 4 haloalkoxy; acetylenyl; or trimethylsilylacetylenyl; R 5 is C 3 -C 5 alkyl; C 4 -C 7 alkenyl; C 3 -C 5 alkynyl; C 3 -C 8 haloalkyl; C 5 -C 8 haloalkenyl; C 3 -C alkoxyalkyl; or phenyl or thienyl each optionally substimted with R 14 and R 15 ; R 6 is C 3 -C 8 alkyl; C 3 -C 7 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 3 -C alkoxyalkyl; or phenyl optionally substimted withR 13 ; and R 14 is methyl; ethyl; methoxy; methylthio; halogen; trifluoromethyl; or N(C r C 2 alkyl) 2 . 7. A compound of Claim 4 wherein: R 3 is halogen; Cj-C 4 alkyl; C C4 haloalkyl; C£-C alkoxy; C j -C 4 haloalkoxy; acetylenyl; or trimethylsilylacetylenyl; R 7 is C 3 -C alkyl; C 4 -C 7 alkenyl; propynyl; C3-C 8 haloalkyl; C3~C 8 haloalkenyl; C3-C 8 alkoxy; C3-C 8 alkoxyalkyl; or phenyl or thienyl each optionally substituted with R 14 and R 15 ; R 9 is C 3 -C 8 alkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; C 3 -C 8 alkoxyalkyl; -NR 12 R 17 ; or R 3 and R 4 are both iodine and R 9 is phenyl optionally substimted with R 14 and R 15 ; and R 14 is methyl; ethyl; methoxy; methylthio; halogen; trifluoromethyl; or N(C r C 2 alkyl) 2 . 8. A compound of Claim 5 wherein: R 1 is C 3 -C 8 alkyl; C 4 -C 8 alkenyl; C 4 -C 8 alkynyl; C 3 -C 8 haloalkyl; or C 3 -C 8 haloalkenyl; R 2 is C 3 -C 8 alkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; or phenyl optionally substimted with R 13 ; R 3 is halogen; and R 4 is hydrogen or halogen. 9. A compound of Claim 6 wherein: R 3 is halogen; R 4 is hydrogen or halogen; R 5 is C 3 -C 5 alkyl; C 4 -C 7 alkenyl; C 3 -C 5 alkynyl; C 3 -C 8 haloalkyl; or C 5 -C 8 haloalkenyl; or phenyl optionally substimted with R 14 and R 15 ; and R 6 is C 3 -C 8 alkyl; C 3 -C 7 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; or phenyl optionally substimted with R 13 . 10. A compound of Claim 7 wherein: R 3 is halogen; R 4 is hydrogen or halogen; R 7 is C 3 -C 8 alkyl; C 4 -C 7 alkenyl; propynyl; C 3 -C 8 haloalkyl; or C 3 -C 8 haloalkenyl; or phenyl optionally substimted with R 14 and R 15 ; and R 9 is C 3 -C 8 alkyl; C 3 -C 8 alkenyl; C 3 -C 8 alkynyl; C 3 -C 8 haloalkyl; C 3 -C 8 haloalkenyl; -NR 12 R 17 ; or R 3 and R 4 are both iodine and R 9 is phenyl optionally substimted with R 14 and R 15 . 11. A compound of Claim 8 which is selected from: 6-bromo-3-propyl-2-propyloxy-4(3H)-quinazolinone; 6,8-diiodo-3-propyl-2-propyloxy-4(3H)-quinazolinone; and 6-iodo-3-propyl-2-propyloxy-4(3H)-quinazolinone. 12. A compound of Claim 10 which is 6,8-diiodo-3-propyl-2-(phenylamino)-4(3H)-quinazolinone. 13. A method for controlling plant diseases caused by fungal plant pathogens comprising applying to the plant or portion thereof to be protected, to the media in which the plant to be protected is growing, or to the plant seed or seedling to be protected an effective amount of a compound of Formula I, H, or UI: wherein: n is 0, 1 or 2; Q i iss i inndueeppeenndαeenπtulyy O υ oorr S_>;; R 1 is C3-C10 alkyl; C3-C5 cycloalkyl; C 4 -C j ø alkenyl; C 4 -CJO alkynyl; CJ- 'C-1K0 haloalkyl; C3-C1 haloalkenyl; C3-C1 haloalkynyl; C 2 -CJO alkoxyalkyl; C 2 -C 10 alkylthioalkyl; C 2 -CIQ al___ylsulfinylalkyl; C 2 -Cκ ) alkylsulfonylalkyl; C5-C10 cycloalkylalkyl; C 4 -CIQ alkenyloxyalkyl; C 4 -CIQ alkynyloxyalkyl; 4-C10 (cycloalkyl)oxyalkyl; C4-CJ Q alkenylthioalkyl; C4-C10 alkynylthioalkyl; Cg-C j ø (cycloalkylthioalkyl; C 2 -CIQ haloalkoxyalkyl; C4-C10 haloalkenyloxyalkyl; C 4 -CIQ haloalkynyloxyalkyl; C -CJ alkoxyalkenyl; C 4 -CIQ alkoxyalkynyl; C -CJO alkylthioalkenyl; C 4 -CJO alkylthioalkynyl; C 4 -CJO trialkylsilylalkyl; CJ-CJQ alkyl substituted with NR- R 12 , nitro, cyano, or phenyl optionally substimted with R 14 , R 15 , an R 16 ; Cj-Ci Q alkoxy; C r C 10 haloalkoxy; C r C 10 alkylthio; C r C 10 haloalkylthio; NR 1 :l R 12 ; or pyridyl, furanyl, thienyl, naphthyl, benzofuranyl, benzothienyl, or quinolinyl each optionally substimted with R 14 , R 15 , and R 1 ; R 2 is C3-C10 alkyl; Cg-C 7 cycloalkyl; C3-C10 alkenyl; C3-C10 alkynyl; Cj-Cio haloalkyl; C3-C10 haloalkenyl; C3-C1 Q haloalkynyl; C 2 -CIQ alkoxyalkyl; C2-C10 alkylthioalkyl; C2-C10 alkylsulfinylalkyl; C2-C10 alkylsulfonylalkyl; C4-C10 cycloalkylalkyl; C 4 -CJO alkenyloxyalkyl; C 4 -CJO alkynyloxyalkyl; C4-C10 (cycloalkyl)oxyalkyl; C 4 -CIQ alkenylthioalkyl; C 4 -CJO alkynylthioalkyl; Cg-C j ø (cycloalkylthioalkyl; C2-C10 haloalkoxyalkyl; C4-C10 haloalkenyloxyalkyl; C 4 -CIQ haloalkynyloxyalkyl; C4-C10 alkoxyalkenyl; C -C- j ø alkoxyalkynyl; C 4 -CJO alkylthioalkenyl; C -CJO alkylthioalkynyl; C 4 -CJO trialkylsilylalkyl; C3-C10 cyanoalkyl; C2-C1 Q nitroalkyl; C r C 10 alkyl substituted with CO 2 R n , NR 1 ^ 12 , or phenyl optionally substimted with R 13 , R 15 , and R 16 ; phenyl optionally substimted with R 13 , R 15 , and R 16 ; -N^R^R 11 ; or -NR^R 12 ; or R 1 and R 2 are taken together to form -CH 2 (CH 2 ) m CH 2 -; m is 1-4; R 3 is halogen; C j -Cg alkyl; C 3 -Cg cycloalkyl; C 2 -Cg alkenyl; C 2 -Cg alkynyl; Cj-Cg haloalkyl; C 3 -Cg haloalkenyl; C 3 -Cg haloalkynyl; C j -Cg alkoxy; C^-Cg haloalkoxy; C 3 -C alkenyloxy; C 3 -C 8 alkynyloxy; C j -C 8 alkylthio; C 3 -C 8 alkenylthio; C 3 -C 8 alkynylthio; C j -Cg alkylsulfinyl; C j -C 8 alkylsulfonyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C 2 -C 8 alkylsulfinylalkyl; C 2 -C 8 alkylsulfonylalkyl; C 4 -C 8 cycloalkylalkyl; C 3 -C 8 trialkylsilyl; nitro; NR n R 12 ; C5-C trialkylsilylalkynyl; or phenyl optionally substimted with at least one R 13 ; R 4 is hydrogen; halogen; C j -C 4 alkyl; C j -C 4 haloalkyl; C j -C 4 alkoxy; or C j -C 4 haloalkoxy; R 5 is C 3 -C 5 alkyl; C 7 -C 10 alkyl; C 4 -C 7 alkenyl; C 3 -C 5 alkynyl; C r C 10 haloalkyl; C5-C10 haloalkenyl; C 3 -CI Q haloalkynyl; C 2 -CI Q alkoxyalkyl other than methoxypropyl; C 2 -CI Q alkylthioalkyl; C 2 -CI Q alkylsulfinylalkyl; C 2 -CJO alkylsulfonylalkyl; C4-C10 cycloalkylalkyl; C 4 -CI Q alkenyloxyalkyl; C 4 -CJO alkynyloxyalkyl; C 4 -CJ Q (cycloalkyl)oxyalkyl; C 4 -CJ alkenylthioalkyl; C 4 -CJO alkynylthioalkyl; C -Cjo (cycloalkyl)thioalkyl; C 2 -CJO haloalkoxyalkyl; C 4 -Cιo haloalkenyloxyalkyl; C 4 -CJO haloalkynyloxyalkyl; C 4 -Cιø alkoxyalkenyl; C 4 -CJO alkoxyalkynyl; C 4 -CI Q alkylthioalkenyl; C4-C10 alkylthioalkynyl; C 4 -CI Q trialkylsilylalkyl; CI-CJ Q alkyl substimted with NR 1 l R 12 , nitro, or phenyl optionally substituted with at least one of R 14 , R 15 , and R 16 ; C 2 -C 10 alkyl substimted with cyano; C r C 10 alkoxy; C 1 -C 10 haloalkoxy; C r C 10 alkylthio; C r C 10 haloalkylthio; NR n R 12 ; or phenyl, furanyl, thienyl, naphthyl, benzof iranyl, or benzothienyl each optionally substimted with R 14 , R 15 , and R 16 ; R 6 is C 3 -C 10 alkyl; C 3 -C 7 alkenyl; C 3 -C 10 alkynyl; C r C 10 haloalkyl; C 3 -C -10 haloalkenyl; C 3 -CI Q haloalkynyl; C 3 -CI alkoxyalkyl other than propoxymethyl; C 2 -Cιø alkylthioalkyl; C 2 -CI Q alkylsulfinylalkyl; C : 2 2-"CCiθ alkylsulfonylalkyl; C 4 -C 1 o cycloalkylalkyl; C 4 -C 10 alkenyloxyalkyl; C 4 - C ιo alkynyloxyalkyl; C 4 -CJO (cycloalkyl)oxyalkyl; C 4 -CJO alkenylthioalkyl; C 4 -C 10 alkynylthioalkyl; C 6 -C 10 (cycloalkyl)thioalkyl; C 2 -C 10 haloalkoxyalkyl; C 4 -Cιo haloalkenyloxyalkyl; C -C*JO haloalkynyloxyalkyl; C4-C10 alkoxyalkenyl; C 4 -CI Q alkoxyalkynyl; C 4 -CI Q alkylthioalkenyl; C 4 -Cιø alkylthioalkynyl; C 4 -Cιø trialkylsilylalkyl; C5-C10 cyanoalkyl; C 2 -Cιø nitroalkyl; or C 3 -C 10 alkyl substituted with CO 2 R π , NR π R 12 , or phenyl optionally substimted with R 13 , R 15 , and R 16 ; or phenyl optionally substimted with R 13 , R 15 , and R 16 ; or R 5 and R 6 are taken together to form -CH 2 (CH 2 ) m CH 2 -; R 7 is C 3 -Cιo alkyl; C -C 7 cycloalkyl; C 4 -C7 alkenyl; propynyl; C5-C10 alkynyl; C 2 -C 10 haloalkyl; C 3 -C 10 haloalkenyl; C 3 -C ø haloalkynyl; C 2 -CJO alkoxyalkyl; C 2 -Cjø alkylthioalkyl; C 2 -CI Q alkylsulfinylalkyl; C 2 -CI Q alkylsulfonylalkyl; C 4 -CJO alkenyloxyalkyl; C 4 -CI Q alkynyloxyalkyl; C4-C10 (cycloalkyl)oxyalkyl; C -C 1Q alkenylthioalkyl; C 4 -CI Q alkynylthioalkyl; Cg-Cjø (cycloalkyl)thioalkyl; C 2 -CJO haloalkoxyalkyl; C -CJO haloalkenyloxyalkyl; C 4 -CI Q haloalkynyloxyalkyl; C 4 -CI Q alkoxyalkenyl; C 4 -CJO alkoxyalkynyl; t-Cjø alkylthioalkenyl; C 4 -CJO alkylthioalkynyl; C 4 -C 10 trialkylsilylalkyl; CJ-CJO alkyl substimted with NR 1:l R 12 or nitro; C 2 -Cιo alkyl substimted with cyano; CJ-CJO alkoxy; CJ-CJO haloalkoxy; CJ-CJO alkylthio; CJ-CJO haloalkylthio; NR 12 R 17 ; or phenyl, pyridyl, furanyl, thienyl, naphthyl, benzofiiranyl, benzothienyl, or quinolinyl each optionally substimted with R 14 , R 15 , and R 16 ; R 8 is hydrogen; C r C 4 alkyl; or -C(=O)R 10 ; R 9 is hydrogen; C 2 -Cιø alkyl; C 3 -C7 cycloalkyl; C 3 -CJO alkenyl; C -C j ø alkynyl; C 3 -Cιo haloalkyl; C 3 -Cιo haloalkenyl; C 3 -Cιo haloalkynyl; C 3 -CJO alkoxyalkyl other than butoxyethyl; C 2 -CI Q alkylthioalkyl; C 2 -CI Q alkylsulfinylalkyl; C 2 -CJO alkylsulfonylalkyl; C4-C10 cycloalkylalkyl; C 4 -C 1 o alkenyloxyalkyl; C4-C1 Q alkynyloxyalkyl; C 4 -CJ Q (cycloalkyl)oxyalkyl; C 4 -C 10 alkenylthioalkyl; C 4 -C 10 alkynylthioalkyl; C 6 -C 10 (cycloalkyl)thioalkyl; C 2 -CI Q haloalkoxyalkyl; C 4 -CI Q haloalkenyloxyalkyl; C 4 -Cιo haloalkynyloxyalkyl; C -CI Q alkoxyalkenyl; C4-C10 alkoxyalkynyl; C4-C10 alkylthioalkenyl; C4-C10 alkylthioalkynyl; C 4 -CJO trialkylsilylalkyl; C r C 10 alkyl substimted with NR 1;l R 12 ; C 4 -C 10 cyanoalkyl; C 2 -C 10 nitroalkyl; Cι-C 8 alkyl substimted with CO 2 R 1:l ; pyridyl, furanyl, thienyl, or naphthyl each optionally substituted with R 14 , R 15 , and R 16 ; -N^R 1 ^ 11 ; -NR 12 R 17 ; -OR 12 ; or -NC(=Q)NR 11 R 12 ; or R 3 and R 4 are both iodine and R 9 is phenyl optionally substituted with R 14 , R 15 , and R 16 ; or R 7 and R 9 are taken together to form -CH 2 (CH 2 ) m CH 2 -; R 10 is hydrogen; C r C 4 alkyl; C r C 4 alkoxy; or NR 1;l R 12 ; R 11 is independently hydrogen; C1-C4 alkyl; or phenyl optionally substituted with at least one R 13 ; R 12 is independently hydrogen; C j -Cg alkyl; or phenyl optionally substimted with at least one R 13 ; or R 11 and R 12 are taken together to form -CH 2 CH 2 CH 2 CH 2 -, -CH 2 (CH 2 ) 3 CH 2 -, -CH 2 CH 2 OCH 2 CH 2 -, -CH 2 CH(Me)CH 2 CH(Me)CH 2 -, or -CH 2 CH(Me)OCH(Me)CH 2 -; R 13 is independently halogen; Cι-C 4 alkyl; C 1 -C alkoxy; C j -C haloalkyl; nitro; or cyano; R 14 is independently C j -Cg alkyl; C^Cg alkoxy; C j -Cg haloalkyl; halogen; C 2 -C 8 alkynyl; C j -Cg thioalkyl; phenyl or phenoxy each optionally substituted with at least one R 13 ; cyano; nitro; -Cg haloalkoxy; C j -C haloalkylthio; C 2 -Cg alkenyl; C 2 -Cg haloalkenyl; acetyl; CO 2 Me; or N(Cι-C 2 alkyl) 2 ; R 15 is independently methyl; ethyl; methoxy; methylthio; halogen; or trifluoromethyl; R 16 is independently halogen; and R 17 is independently Cι~C 8 alkyl; or phenyl optionally substimted with at least one R 13 ; or an N-oxide or agriculturally-suitable salt thereof. 14. A fimgicidal composition comprising an effective amount of a compound of Formula I, H, or HI: wherein: n is 0, 1 or 2; Q is independently O or S; R 1 is C 3 -C 10 alkyl; C 3 -C 5 cycloalkyl; C 4 -C 10 alkenyl; C 4 -C 10 alkynyl; C C-io haloalkyl; C 3 -CI Q haloalkenyl; C -CJO haloalkynyl; C 2 -CI Q alkoxyalkyl; C 2 -Cιo alkylthioalkyl; C 2 -CJO alkylsulfinylalkyl; C 2 -CI Q alkylsulfonylalkyl; C5-C10 cycloalkylalkyl; C 4 -CJO alkenyloxyalkyl; C 4 -Cχo alkynyloxyalkyl; C4-C10 (cycloalkyl)oxyalkyl; C4-C10 alkenylthioalkyl; C 4 -CJO alkynylthioalkyl; Cg-C^o (cycloalkylthioalkyl; C 2 -CI Q haloalkoxyalkyl; C -CJO haloalkenyloxyalkyl; C4-C10 haloalkynyloxyalkyl; C 4 -CJ Q alkoxyalkenyl; C 4 -CI Q alkoxyalkynyl; C 4 -CI Q alkylthioalkenyl; C 4 -CJ Q alkylthioalkynyl; C 4 -CI Q trialkylsilylalkyl; CJ-CJ alkyl substimted with NR 1:l R 12 , nitro, cyano, or phenyl optionally substituted with R 14 , R 15 , and R 16 ; C r C 10 alkoxy; C r C 10 haloalkoxy; C r C 10 alkylthio; C r C 10 haloalkylthio; NR 1 ;l R 12 ; or pyridyl, furanyl, thienyl, naphthyl, benzofuranyl, benzothienyl, or quinolinyl each optionally substituted with R 14 , R 15 , and R 2 is C 3 -C 10 alkyl; Cg-C 7 cycloalkyl; C 3 -C 10 alkenyl; C 3 -C!ø alkynyl; CJ-CJ Q haloalkyl; C3-C10 haloalkenyl; C3-C10 haloalkynyl; C 2 -CI Q alkoxyalkyl; 2 -Cιø alkylthioalkyl; C 2 -CI Q alkylsulfinylalkyl; C 2 -CI Q alkylsulfonylalkyl; 4-C10 cycloalkylalkyl; C 4 -CI Q alkenyloxyalkyl; C 4 -C j ø alkynyloxyalkyl; C4-C10 (cycloalkyl)oxyalkyl; C4-C10 alkenylthioalkyl; C 4 -CI Q alkynylthioalkyl; Cg-CjQ (cycloalkylthioalkyl; C 2 -CI Q haloalkoxyalkyl; C 4 -C 10 haloalkenyloxyalkyl; C 4 -Cιo haloalkynyloxyalkyl; C 4 -Cιø alkoxyalkenyl; C 4 -CJ Q alkoxyalkynyl; C4-C10 alkylthioalkenyl; C -CI alkylthioalkynyl; C 4 -CI Q trialkylsilylalkyl; C3-C10 cyanoalkyl; C 2 -CI Q nitroalkyl; C r C 10 alkyl substimted with CO 2 R π , NR 1 ;l R 12 , or phenyl optionally substimted with R 13 , R 15 , and R 16 ; phenyl optionally substituted with R 13 , R 15 , and R 16 ; -NOR-WR 11 ; or -NR π R 12 ; or R 1 and R 2 are taken together to form -CH 2 (CH 2 ) m CH 2 -; m is 1-4; R 3 is halogen; Cj-C 8 alkyl; C 3 -C 8 cycloalkyl; C 2 -C 8 alkenyl; C 2 -C 8 alkynyl; C j -C 8 haloalkyl; C3-C 8 haloalkenyl; C3-C haloalkynyl; C j -C alkoxy; C j -C 8 haloalkoxy; C3-C 8 alkenyloxy; C3-C 8 alkynyloxy; Cj-Cg alkylthio; C 3 -C 8 alkenylthio; C 3 -C 8 alkynylthio; C r C 8 alkylsulfinyl; C r C 8 alkylsulfonyl; C 2 -C 8 alkoxyalkyl; C 2 -C 8 alkylthioalkyl; C 2 -C 8 alkylsulfinylalkyl; C 2 -C 8 alkylsulfonylalkyl; C 4 -C 8 cycloalkylalkyl; C 3 -C 8 trialkylsilyl; nitro; NR-^R 12 ; C5~C 8 trialkylsilylalkynyl; or phenyl optionally substimted with at least one R 13 ; R 4 is hydrogen; halogen; C r C alkyl; C C 4 haloalkyl; Cj-C alkoxy; or C j -C haloalkoxy; R 5 is C 3 -C 5 alkyl; C 7 -C 10 alkyl; C 4 -C 7 alkenyl; C 3 -C 5 alkynyl; C r C 10 haloalkyl; C5-C10 haloalkenyl; C 3 -CI Q haloalkynyl; C 2 -C o alkoxyalkyl other than methoxypropyl; C 2 -CIQ alkylthioalkyl; C 2 -Cιo alkylsulfinylalkyl; C 2 -CI Q alkylsulfonylalkyl; C 4 -CIQ cycloalkylalkyl; C 4 -CJO alkenyloxyalkyl; C 4 -CJO alkynyloxyalkyl; C 4 -CI Q (cycloalkyloxyalkyl; C 4 -CI alkenylthioalkyl; C 4 -CJO alkynylthioalkyl; Cg-Cjo (cycloalkylthioalkyl; C 2 -CJO haloalkoxyalkyl; C 4 -CJO haloalkenyloxyalkyl; C 4 -CI haloalkynyloxyalkyl; C4-C10 alkoxyalkenyl; C -CJ Q alkoxyalkynyl; C 4 -CI Q alkylthioalkenyl; C 4 -Cιo alkylthioalkynyl; C 4 -CJO trialkylsilylalkyl; CJ-CJO alkyl substimted with NR-^R 12 , nitro, or phenyl optionally substimted with at least one of R 14 , R 15 , and R 16 ; C 2 -C 10 alkyl substimted with cyano; C r C 10 alkoxy; C r C 10 haloalkoxy; C r C 10 alkylthio; C r C 10 haloalkylthio; NR-WR 12 ; or phenyl, furanyl, thienyl, naphthyl, benzofuranyl, or benzothienyl each optionally substimted with R 14 , R 15 , and R 16 ; R 6 is C 3 -C 10 alkyl; C 3 -C 7 alkenyl; C 3 -C 10 alkynyl; C r C 10 haloalkyl; C 3 -C 10 haloalkenyl; C^CJ Q haloalkynyl; C 3 -CI Q alkoxyalkyl other than propoxymethyl; C 2 -CI Q alkylthioalkyl; C 2 -CI Q alkylsulfinylalkyl; C 2 -CJ alkylsulfonylalkyl; C 4 -CJO cycloalkylalkyl; C 4 -CI Q alkenyloxyalkyl; C 4 -CIQ alkynyloxyalkyl; C 4 -Cιo (cycloalkyl)oxyalkyl; C 4 -CI Q alkenylthioalkyl; C 4 -C 10 alkynylthioalkyl; C 6 -C 10 (cycloalkyl)thioalkyl; C 2 -C 10 haloalkoxyalkyl; C 4 -CI Q haloalkenyloxyalkyl; C 4 -C- j ø haloalkynyloxyalkyl; C 4 -CJO alkoxyalkenyl; C 4 -Cjø alkoxyalkynyl; C 4 -CJ Q alkylthioalkenyl; C 4 -Cιo alkylthioalkynyl; C 4 -CJO trialkylsilylalkyl; C5-C10 cyanoalkyl; C 2 -Cιo nitroalkyl; or C 3 -C 10 alkyl substimted with CO 2 R π , NR 1 :l R 12 , or phenyl optionally substimted with R 13 , R 15 , and R 16 ; or phenyl optionally substimted with R 13 , R 15 , and R 16 ; or R 5 and R 6 are taken together to form -CH 2 (CH 2 ) m CH 2 -; R 7 is C 3 -C 10 alkyl; C 3 -C 7 cycloalkyl; C -C 7 alkenyl; propynyl; C5-C10 alkynyl; C 2 -CJO haloalkyl; C 3 -CJQ haloalkenyl; C3-C1Q haloalkynyl; C 2 -CJO alkoxyalkyl; C 2 -CJO alkylthioalkyl; C 2 -CI Q alkylsulfinylalkyl; C 2 -CJO alkylsulfonylalkyl; C 4 -CI Q alkenyloxyalkyl; C 4 -CI Q alkynyloxyalkyl; C4-C10 (cycloalkyl)oxy alkyl; C 4 -C j Q alkenylthioalkyl; C 4 -C j Q alkynylthioalkyl; Cg-Cjo (cycloalkyl)thioalkyl; C 2 -CJO haloalkoxyalkyl; C 4 -CJO haloalkenyloxyalkyl; C 4 -Cχo haloalkynyloxyalkyl; C4-C10 alkoxyalkenyl; C4-C10 alkoxyalkynyl; C4-C1 alkylthioalkenyl; C4-C10 alkylthioalkynyl; C -C 10 trialkylsilylalkyl; C r C 10 alkyl substimted with NR n R 12 or nitro; C 2 -Cιo alkyl substimted with cyano; CJ-C-JO alkoxy; CJ-CJO haloalkoxy; Cj-Cio alkylthio; CJ-CI Q haloalkylthio; NR 12 R 17 ; or phenyl, pyridyl, furanyl, thienyl, naphthyl, benzofuranyl, benzothienyl, or quinolinyl each optionally substituted with R 14 , R 15 , and R 16 ; R 8 is hydrogen; C r C 4 alkyl; or -C(=O)R 10 ; R 9 is hydrogen; C 2 -C 10 alkyl; C 3 -C 7 cycloalkyl; C 3 -C 10 alkenyl; C 3 -C 10 alkynyl; C 3 -CJO haloalkyl; C 3 -C*to haloalkenyl; C 3 -Cιo haloalkynyl; C 3 -CJO alkoxyalkyl other than butoxyethyl; C 2 -CI Q alkylthioalkyl; C 2 -CIQ alkylsulfinylalkyl; C 2 -CI Q alkylsulfonylalkyl; C 4 -CJO cycloalkylalkyl; C 4 -C^o alkenyloxyalkyl; C -CJO alkynyloxyalkyl; C 4 -C*ιo (cycloalkyl)oxyalkyl; C -C 10 alkenylthioalkyl; C -C 10 alkynylthioalkyl; Cg-C 10 (cycloalkyl)thioalkyl; C -C 1( ) haloalkoxyalkyl; C 4 -C 10 haloalkenyloxyalkyl; C -Cκ ) haloalkynyloxyalkyl; C4-C10 alkoxyalkenyl; C -CJO alkoxyalkynyl; C 4 -C 10 alkylthioalkenyl; Q-CJ Q alkylthioalkynyl; C 4 -Cχo trialkylsilylalkyl; C r C 10 alkyl substimted with NR-^R 12 ; C 4 -C 10 cyanoalkyl; C 2 -C 10 nitroalkyl; Cι~C 8 alkyl substituted with CO 2 R 1 :l ; pyridyl, furanyl, thienyl, or naphthyl each optionally substimted with R 14 , R 15 , and R 16 ; -N=CR 11 R 11 ; -NR 12 R 17 ; -OR 12 ; or -NC(=Q)NR 11 R 12 ; or R 3 and R 4 are both iodine and R 9 is phenyl optionally substituted with R 14 , R 15 , and R 16 ; or R 7 and R 9 are taken together to form -CH 2 (CH 2 ) m CH 2 -; R 10 is hydrogen; C -C 4 alkyl; C r C 4 alkoxy; or NR-^R 12 ; R 11 is independently hydrogen; Cι-C 4 alkyl; or phenyl optionally substimted with at least one R 13 ; R 12 is independently hydrogen; C r C 8 alkyl; or phenyl optionally substituted with at least one R 13 ; or R 11 and R 12 are taken together to form -CH 2 CH 2 CH 2 CH 2 -, -CH 2 (CH 2 ) 3 CH 2 -, -CH 2 CH 2 OCH 2 CH 2 -, -CH 2 CH(Me)CH 2 CH(Me)CH 2 -, or -CH 2 CH(Me)OCH(Me)CH 2 -; R 13 is independently halogen; C!-C 4 alkyl; C j -C alkoxy; C j - haloalkyl; nitro; or cyano; R 14 is independently C j -Cg alkyl; Cj-Cg alkoxy; C j -Cg haloalkyl; halogen; C 2 -C 8 alkynyl; C^-Cg thioalkyl; phenyl orphenoxy each optionally substimted with at least one R 13 ; cyano; nitro; C r Cg haloalkoxy; Cj-Cg haloalkylthio; C 2 -C 6 alkenyl; C 2 -C 6 haloalkenyl; acetyl; CO 2 Me; or N(C r C 2 alkyl) 2 ; R 15 is independently methyl; ethyl; methoxy; methylthio; halogen; or trifluoromethyl; R 16 is independently halogen; and R 17 is independently C j -Cg alkyl; or phenyl optionally substimted with at least one R 13 ; or an N-oxide or agriculturally-suitable salt thereof; and at least one of (a) a surfactant, (b) an organic solvent, and (c) at least one solid or liquid diluent. 15. A method for controlling wheat powdery mildew comprising applying to the plant or portion thereof to be protected, to the media in which the plant to be protected is growing, or to the plant seed or seedling to be protected an effective amount of a compound of Claim 1.

Inventors: BEREZNAK JAMES FRANCIS, CHANG ZEN-YU, SELBY THOMAS PAUL, STERNBERG CHARLENE GROSS, BEREZNAK, JAMES, FRANCIS, CHANG, ZEN-YU, SELBY, THOMAS, PAUL, STERNBERG, CHARLENE, GROSS
Applicants: BEREZNAK JAMES FRANCIS, CHANG ZEN YU, DU PONT, SELBY THOMAS PAUL, STERNBERG CHARLENE GROSS, BEREZNAK, JAMES, FRANCIS, CHANG, ZEN-YU, E.I. DU PONT DE NEMOURS AND COMPANY, SELBY, THOMAS, PAUL, STERNBERG, CHARLENE, GROSS
Application year: 1994
Main classification: C07D239
IPC codes: A01N43, A01P3, C07D239, C07D401, C07D405, C07D409